Roadside Attractions + Route 66
Booked hotels
- Oct 1–3: Homewood Suites Indianapolis Downtown IUPUI — Free hot breakfast MapHotel
- Oct 3: Eighteen-Ninety Sleepover — No confirmed hotel breakfast MapHotel
- Oct 4: Spark by Hilton Springfield Southwest — Free continental breakfast MapHotel
- Oct 5: Quality Inn Pontiac — Free continental breakfast MapHotel
- Oct 6: Fairfield Inn & Suites Joliet North/Plainfield — Free hot breakfast MapHotel
- Oct 7: Grant Park Hotel — No free breakfast MapHotel
- Oct 8: Wingate South Bend/Notre Dame — Free breakfast MapHotel
Restaurant plan
| Date | Time | Restaurant | Status / backup plan | Link |
|---|---|---|---|---|
| Thu Oct 1 | 7:45 PM | Slippery Noodle Inn | Call 6:45–7:00; fallback Yard House if 30–40+ min wait | Restaurant |
| Fri Oct 2 | 7:30 PM | Weber Grill | BOOKED — OpenTable | Restaurant |
| Sat Oct 3 | 6:45 PM CT | Richards Farm | BOOKED | Restaurant |
| Sun Oct 4 | 7:00 PM CT | Route 66 Motorheads | Call ~6:15; fallback Westwoods if 25–30+ min wait | Restaurant |
| Mon Oct 5 | 6:40 PM CT | Route 66 RoadHouse | Call ~5:45; fallback Baby Bull’s if not seated by ~7 | Restaurant |
| Tue Oct 6 | 7:30 PM CT | Metro Grill & Bar | Call ~6:45; fallback Heroes West if 20–25+ min wait | Restaurant |
| Wed Oct 7 | 8:15 PM CT | Acanto | BOOKED — OpenTable | Restaurant |
| Thu Oct 8 | 8:30 PM ET | Fiddler’s Hearth | BOOKED — Toast | Restaurant |
Tickets & timed entries
| Date | Time | Attraction | Price | Status | Link |
|---|---|---|---|---|---|
| Fri Oct 2 | 9:00 AM | Indianapolis Motor Speedway Museum | $25 adult / $23 senior 55+ | PURCHASED — museum admission secured. | Tickets / info |
| Fri Oct 2 | During 9:00–11:30 AM block | Kiss the Bricks track tour | Pending / price per IMS confirmation | Email pending after reservation mix-up | Tour info |
| Fri Oct 2 | 2:55 PM | Soldiers & Sailors Monument observation level | $10 adult / $5 senior 60+ | Buy on site; Friday hours currently to 4 PM. | Tickets / info |
| Sun Oct 4 | 3:00 PM | Dana-Thomas House | FREE; donation encouraged | Reserve ahead; tour capacity 15. | Tickets / info |
| Mon Oct 5 | Morning | Lincoln Home | FREE | Same-day timed ticket at Visitor Center only. | Tickets / info |
| Mon Oct 5 | 10:15 AM | Lincoln Presidential Museum | $15 adult / $12 senior 62+ | PURCHASED — tickets in Apple Wallet. | Tickets / info |
| Tue Oct 6 | 3:45 PM | Illinois Rock & Roll Museum | $10 adult / $7 senior 65+ | Pay on arrival. | Tickets / info |
| Wed Oct 7 | 10:00 AM | Old Joliet Prison — self-guided | $22 | PURCHASED — self-guided tickets in Apple Wallet. | Tickets / info |
| Wed Oct 7 | 11:45 AM | Joliet Area Historical Museum | $10 adult / $9 senior 60+ | Pay on arrival. | Tickets / info |
| Wed Oct 7 | 5:30 PM | Skydeck Chicago | PURCHASED | Ticket already bought. | Tickets / info |
| Thu Oct 8 | Chicago transit | CTA/Pace 1-Day Ventra Ticket | $5 per person | Buy at Ventra vending machine; good for 24 hours from first use. | Tickets / info |
| Thu Oct 8 | 5:20 PM | Indiana Dunes National Park | $25 per vehicle | No timed reservation; pass valid 7 days. | Tickets / info |
Google Maps route buttons
Day 1: Thu Oct 1, 2026Mentor → Dresden → Frazeysburg → Newark → Springfield → Indianapolis
| Time | Stop | Time there | Notes |
|---|---|---|---|
6:30 AM ET |
— |
The early departure is intentional and gives you enough daylight for the three Longaberger stops, Springfield and Vandalia before the long US 40 run into Indianapolis. Day 1 is a longer day, but much of that extra clock time is spent eating or walking around rather than simply sitting behind the wheel. |
|
8:00–8:35 AM ET |
35 min |
This is your first road-trip breakfast and it lands about 90 minutes after leaving Mentor, which is the rhythm you wanted. Keep it comfortable but fairly quick so the three Longaberger stops stay on schedule. |
|
9:20–9:40 AM ET |
20 min |
Before the famous Newark headquarters, Longaberger operated from this wonderfully literal basket-shaped building in Dresden. It gives you the first piece of the Longaberger story and makes a natural exterior-photo stop before the larger Apple Basket and Big Basket Building farther west. |
|
9:55–10:20 AM ET |
25 min |
The apple-filled basket at the former Longaberger Homestead is exactly the sort of giant roadside object this trip was built for. Mostly a hop-out, walk-around and photograph stop, but seeing it between the Dresden basket and the Newark headquarters turns the morning into a little three-stop Longaberger history trail. Allow about 25 minutes here before continuing to Newark. |
|
10:45–11:15 AM ET |
30 min |
One of Ohio's most recognizable novelty buildings: a seven-story office building shaped like a gigantic Longaberger market basket. Plan on exterior photos from several angles rather than a long visit, and enjoy it as the grand finale of the morning's three Longaberger stops. |
|
12:45–1:10 PM ET |
25 min |
This is deliberately flexible. The default is a quick snack or coffee so lunch doesn't eat up the afternoon, but if you're genuinely hungry, Casa Centro remains the full-meal fallback. Either way, try to keep the stop inside the noon-to-2 window you prefer. |
|
1:20–2:05 PM ET |
45 min |
Our replacement for the incorrectly identified root-beer mug turned out to be a better roadside-Americana stop anyway: a detailed folk-art world of miniature buildings, figures and stone constructions created in a residential yard. |
|
2:50–3:35 PM ET |
45 min |
A real walking stop rather than a windshield photo. Give yourselves time to wander among the large outdoor sculptures and stretch your legs before the US 40 drive. |
|
Route control ET |
— |
This is where the trip deliberately chooses the old National Road over I-70. Turn on Google Maps' Avoid Highways option, inspect the blue route before starting, and make sure it stays on US 40 through Richmond and Cambridge City. Cambridge City is still recovering from the August flooding, so allow a little extra patience for local repairs or temporary traffic control. |
|
Route control ET |
— |
Continue west on historic US 40 rather than letting navigation pull you toward I-70. Greenfield is included as a control point because it gives Maps another reason to keep you on the National Road, and it also keeps the day's travel connected to the older highway rather than the interstate. |
|
5:40–5:55 PM ET |
15 min |
A wonderfully shameless roadside photo stop: a large pink elephant outside Elite Beverages. This is the Fortville elephant, not Shipshewana. Keep this to about 15 minutes so hotel check-in and dinner stay comfortable. |
|
~6:45 PM ET |
— |
BOOKED for October 1–3. The downtown/IUPUI location works well for the Canal Walk and keeps Friday's Indianapolis circuit compact. The free hot breakfast both mornings also removes two separate restaurant stops from the itinerary. |
|
7:45 PM ET |
75 min |
A casual first-night dinner with real Indianapolis music history and atmosphere. The Slippery Noodle dates to 1850 and has long been associated with live blues, so the meal doubles as a music stop. Call around 6:45–7:00 PM; if the quoted wait is over roughly 30–40 minutes, use Yard House as the backup rather than sacrificing the evening to a restaurant line. |
Day 2: Fri Oct 2, 2026Indianapolis
| Time | Stop | Time there | Notes |
|---|---|---|---|
6:45–7:15 AM ET |
30 min |
Use the hotel's included breakfast and keep it light and fast. The point is to get coffee and enough food to start the day without turning breakfast into another scheduled attraction or spoiling the fuller lunch later on. |
|
7:35–8:20 AM ET |
45 min |
Walk a scenic piece of the downtown canal rather than treating the full three-mile loop as an obligation. This gives you water, skyline and public-art views without stealing the morning from the Speedway. |
|
9:00–11:30 AM ET |
2 hr 30 min |
This is one of the trip's true destination attractions, not a quick roadside stop. Give the renovated museum the full block for the cars, racing history and gift shop. MUSEUM TICKETS ARE PURCHASED. You are also trying to add the Kiss the Bricks track tour inside this same window; an email is pending with the Speedway after the reservation mix-up, so keep the 9:00–11:30 block intact until that is resolved. |
|
11:45 AM–12:20 PM ET |
35 min |
A classic old-school drive-in and a natural post-Speedway lunch. House root beer makes this a much better place to scratch the root-beer itch than the attraction we originally misidentified in Springfield, Ohio. |
|
12:45–1:00 PM ET |
15 min |
Three enormous office buildings designed as stepped pyramids. This one is intentionally short: park where permitted, get the geometric photos, and move on. |
|
1:15–2:00 PM ET |
45 min |
The centerpiece is the Ruins, a dramatic assemblage built around rescued New York skyscraper sculptures. An hour gives you time for the Ruins and a little of the surrounding park without turning the day into a hike. |
|
2:15–2:40 PM ET |
25 min |
The delightfully distorted little house is back in the Art Center's ArtsPark after renovations. It is the sort of optical oddity that photographs far better when you walk around it instead of shooting it from one angle. |
|
2:55–3:45 PM ET |
50 min |
Spend time on Monument Circle itself, then go up inside the Soldiers & Sailors Monument now that the observation level has reopened. The upper view turns this from a street-level photo stop into one of the best downtown panoramas of the trip. Current Friday hours run 10 AM–4 PM; admission is currently $10 adult / $5 senior 60+ and is purchased on site. |
|
3:55–4:10 PM ET |
15 min |
A compact music-history stop at the former Market Square Arena site, commemorating Elvis Presley's final concert on June 26, 1977. |
|
4:25–5:10 PM ET |
45 min |
Crown Hill is huge, so go in knowing the destination: President Benjamin Harrison is in Lot 57, Section 13. The cemetery itself is handsome enough that the drive through is part of the stop. |
|
~5:30 PM ET |
— |
Rest before dinner. |
|
7:30 PM ET |
90 min |
Your Indianapolis Friday-night dinner is locked in here. Weber Grill gives you a real sit-down dinner without pushing the meal into steakhouse-splurge territory, and the downtown location works nicely after the afternoon attractions and hotel break. RESERVATION BOOKED through OpenTable. |
|
After dinner ET |
20 min |
If the projection program is operating that evening, loop back after dinner. It is an easy optional flourish because you are already downtown. |
Day 3: Sat Oct 3, 2026Indianapolis → Franklin → US 40 → Terre Haute → Marshall → Casey
| Time | Stop | Time there | Notes |
|---|---|---|---|
6:45–7:15 AM ET |
30 min |
Use the hotel's included breakfast and keep it light and fast. The point is to get coffee and enough food to start the day without turning breakfast into another scheduled attraction or spoiling the fuller lunch later on. |
|
7:30 AM ET |
— |
Breakfast at the hotel, check out, and start your principal US 40 day. Keep I-70 off the menu. |
|
8:15–8:30 AM ET |
15 min |
Nancy Kerlin Barnett's grave was famously left in the middle of the road when the road was built around the family burial plot. The shoulder is limited, so this is a see-it-only-if-you-can-stop-safely attraction. |
|
8:45–9:00 AM ET |
15 min |
A giant rocking chair outside Long's Furniture. Exactly the kind of ten-minute photograph that keeps a roadside trip delightfully peculiar. |
|
Route control ET |
— |
Turn on Avoid Highways and verify US 40 before starting this leg. Plainfield is a routing control point, not an attraction stop. Turn on Avoid Highways and verify US 40. |
|
Route control ET |
— |
Stay on the historic National Road west toward Terre Haute. Do not accept an I-70 reroute. Remain on the National Road; do not accept an I-70 reroute. |
|
11:40 AM–12:35 PM ET |
55 min |
Terre Haute has a large public-mural collection. Instead of chasing every wall, park downtown, eat, and walk a compact cluster such as Arts Alley and nearby pieces. Keep the meal light by default; M. Mogger’s is the full-lunch option if you are hungry. |
|
12:10–12:30 PM CT |
20 min |
After crossing into Illinois, move your clocks back one hour. The enormous gavel stands at the Clark County Courthouse and is a wonderfully efficient 'we have to photograph that' stop. You gain one hour crossing into Illinois, so the clock now switches to Central Time. |
|
12:40–1:05 PM CT |
25 min |
A surviving brick section of the National Road makes the US 40 theme tangible. Drive it slowly and get out for a few photographs where safe. |
|
1:40–5:30 PM CT |
3 hr 50 min |
This is the giant-object mother lode: rocking chair, mailbox, wind chime, pitchfork, golf tee, wooden shoes and more. Start with the walkable downtown cluster, then use the car for the scattered giants. Do not reduce twelve absurdly large objects to a ten-minute checklist. |
|
5:35 PM CT |
— |
BOOKED. A small historic hotel right in the middle of Casey, so after checking in you can still wander back out for evening photos if the mood strikes. BOOKED for the night of October 3. |
|
6:45 PM CT |
75 min |
A longtime Casey restaurant in a converted barn, complete with its own giant-scale personality. It fits the day better than a generic chain dinner. RESERVATION BOOKED for Oct. 3. |
Day 4: Sun Oct 4, 2026Casey → Champaign → Vandalia → Springfield
| Time | Stop | Time there | Notes |
|---|---|---|---|
8:00–8:30 AM CT |
30 min |
Eighteen-Ninety does not clearly advertise a regular breakfast service, so the easy solution is right across the street. Reflections gives you a proper Sunday breakfast without adding driving or parking logistics, and its location lets you step back out onto the road immediately afterward. |
|
8:30 AM CT |
— |
Leave Casey after breakfast with the 3:00 PM Dana-Thomas House tour as the day's fixed anchor. The route deliberately uses the morning for Humpty Dumpty and the Kaskaskia Dragon, then works west into Springfield with enough cushion to arrive at the Wright house before tour time. |
|
10:00–10:15 AM CT |
15 min |
A giant Humpty Dumpty perched outside the Esquire Lounge. This is a pure hop-out-and-grin photo stop before turning back southwest. |
|
12:10–12:30 PM CT |
20 min |
The giant metal dragon is one of the trip's wonderfully unnecessary roadside creations, and the fun part is making it breathe fire. Stop first at Kaskaskia Supply for $1 dragon tokens; Sunday hours are currently 10 AM–5 PM. Buy 3–4 tokens so you have more than one chance to capture the short burst of flame in photos or video. |
|
12:30–12:55 PM CT |
25 min |
Keep this midday stop deliberately light by default so the 3:00 PM Dana-Thomas House reservation stays comfortable. If breakfast has worn off and you want a full lunch, that is fine, but choose something quick enough to be back on the road by about 1:00 PM. |
|
2:45 PM CT |
15 min |
Arrive a few minutes early so parking, check-in and finding the tour entrance never become part of the drama. This buffer is intentionally separate from the tour itself because the house limits group size and the 3:00 PM reservation is the day's hard appointment. |
|
3:00–4:00 PM CT |
60 min |
Your Frank Lloyd Wright stop and one of the architectural highlights of the trip. The remarkable 1902 house preserves one of the largest intact collections of Wright-designed art glass, furniture and interior details, so this deserves to be experienced inside rather than treated as a drive-by. The guided tour is free, donations are encouraged, and tours are limited to 15 people. |
|
4:15–4:50 PM CT |
35 min |
Visit Lincoln's monumental final resting place in Oak Ridge Cemetery. Give yourselves enough time to go inside rather than merely photographing the obelisk from the car. Go inside rather than making this only an exterior photo. |
|
5:15–6:00 PM CT |
45 min |
A 1.25-mile hand-laid brick alignment of old Route 66. This is one of those stops where the road itself is the attraction, so drive it rather than just photographing the sign. Try to reach it while there is still useful evening light. |
|
~6:25 PM CT |
— |
BOOKED. Check in before dinner; the southwest location is convenient for the Auburn return and the evening Motorheads run. BOOKED. Free continental breakfast Monday morning. |
|
7:00–8:15 PM CT |
75 min |
Your preferred Springfield dinner choice, and I agree with it. The restaurant is wrapped in Route 66, automotive and music memorabilia, so dinner doubles as another attraction rather than interrupting the theme. Call around 6:15 PM. If the wait is over 25–30 minutes, use Westwoods Lodge as the fallback. |
|
8:30–9:15 PM CT |
45 min |
A walk-through miniature tour of Illinois Route 66 with signs, replicas and neon. After dark is exactly when the neon earns its keep. |
Day 5: Mon Oct 5, 2026Springfield → Atlanta → Pontiac
| Time | Stop | Time there | Notes |
|---|---|---|---|
7:45–8:05 AM CT |
20 min |
Use the hotel's included breakfast and keep it light and fast. The point is to get coffee and enough food to start the day without turning breakfast into another scheduled attraction or spoiling the fuller lunch later on. |
|
8:35–9:00 AM CT |
25 min |
Arrive around opening time and get free same-day timed tickets. This keeps you from discovering at noon that the tour you wanted has already filled. Pick up FREE same-day timed tour tickets in person; they cannot be reserved ahead. |
|
9:00–10:00 AM CT |
60 min |
Tour the only home Abraham Lincoln ever owned and then spend a few minutes in the preserved four-block neighborhood. The surrounding streets make the site feel much more complete than a single restored house. |
|
10:15 AM–12:45 PM CT |
2 hr 30 min |
Give the museum the full block rather than trying to skim it. The exhibits combine original artifacts, immersive galleries and theatrical presentations to tell Lincoln's life and presidency in a much more experiential way than a traditional display-case museum. TICKETS ARE PURCHASED and stored in Apple Wallet. |
|
1:00–1:50 PM CT |
50 min |
A classic Mother Road lunch and the home associated with the Cozy Dog on a Stick. The walls, Route 66 memorabilia and Bob Waldmire connection are as important to this trip as the food. |
|
2:40–3:35 PM CT |
55 min |
A museum devoted to Muffler Men and their fiberglass relatives. Since you've already been hunting giant people and objects, this is practically graduate school for the trip. |
|
3:35–4:10 PM CT |
35 min |
Atlanta's famous Muffler Man holds a hot dog instead of an axe. Walk the compact downtown for murals and Route 66 details while you're there. |
|
5:10–6:05 PM CT |
55 min |
Excellent timing: Pontiac's new Route 66 Centennial Plaza is scheduled to open September 18, 2026, just before your trip. Pair it with the huge shield mural, Bob Waldmire imagery and the downtown mural walk while daylight remains. Outdoor Pontiac portion, including the new Route 66 Centennial Plaza scheduled to open Sept. 18, 2026, just before your trip. |
|
6:15–6:30 PM CT |
15 min |
BOOKED. Check in after the downtown walk, then choose dinner based on how ambitious you still feel. BOOKED. Free continental breakfast Tuesday morning. |
|
6:40–7:45 PM CT |
65 min |
This is the definite Pontiac dinner and keeps the Mother Road theme going after the murals and Centennial Plaza. Because Monday closing is 8 PM, call around 5:45 PM while you're already in Pontiac. If they cannot seat you by about 7:00, switch to Baby Bull's near the hotel rather than letting dinner become a late-night bottleneck. |
Day 6: Tue Oct 6, 2026Pontiac → Odell → Dwight → Gardner → Braidwood → Wilmington → Joliet
| Time | Stop | Time there | Notes |
|---|---|---|---|
7:30–7:50 AM CT |
20 min |
Use the hotel's included breakfast and keep it light and fast. The point is to get coffee and enough food to start the day without turning breakfast into another scheduled attraction or spoiling the fuller lunch later on. |
|
9:00–10:15 AM CT |
75 min |
This is the indoor half of your Pontiac visit: Illinois Route 66 history, memorabilia, Bob Waldmire material and the culture surrounding the Mother Road. Monday evening handles the outdoor pieces so the museum can have your attention this morning. |
|
10:35–11:00 AM CT |
25 min |
A restored 1932 Standard Oil station, now a village welcome center. The tiny scale and white-and-green cottage design feel like Route 66 frozen in amber. |
|
11:20–11:45 AM CT |
25 min |
Another beautifully restored filling station, notable for having served motorists for 66 years. It is now a visitor center and pairs naturally with Odell without much backtracking. |
|
12:00–12:50 PM CT |
50 min |
A simple road-food stop with the right address and the right theme. This keeps lunch on the Mother Road rather than surrendering to a highway exit chain. |
|
1:10–1:30 PM CT |
20 min |
A tiny 1906 jail with exactly what the name advertises. You can step behind the bars, get the obligatory inmate photograph and be back on Route 66 in twenty minutes. |
|
1:45–2:15 PM CT |
30 min |
The restaurant grounds are populated by larger-than-life Elvis, Marilyn Monroe, Superman and Blues Brothers figures. You have just eaten, so treat this as a photo stop unless a shake somehow finds room. |
|
2:35–3:10 PM CT |
35 min |
The 30-foot astronaut Muffler Man has been restored and now stands at South Island Park with a Route 66 monument and dedicated photo area. This is one of the defining fiberglass icons of Illinois Route 66. |
|
3:45–4:45 PM CT |
60 min |
A particularly good match for you: Illinois music history sitting directly on Route 66. Current hours run to 5 PM, so this stop is deliberately placed before the outdoor Joliet pieces. Current admission: $10 adult / $7 senior 65+; pay on arrival. Current admission is $10 adult / $7 senior 65+; pay on arrival. |
|
4:50–5:10 PM CT |
20 min |
The ornate 1926 theater is one of downtown Joliet's visual showpieces. No tour needed; photograph the façade and marquee, then keep moving. |
|
5:20–5:50 PM CT |
30 min |
A former ice-cream stand turned Route 66 photo stop, topped by Jake and Elwood. The adjoining park also gives you a look toward the old Joliet prison, tying two of the next day's themes together. |
|
6:00–6:20 PM CT |
20 min |
A quick look at an elaborate 1873 Renaissance Revival mansion. This is intentionally an exterior bonus, not another tour. |
|
~6:45 PM CT |
Fairfield Inn & Suites Joliet North/Plainfield 3239 Norman Ave, Joliet, IL 60435 |
— |
BOOKED. The hotel is outside downtown, so finish the downtown attractions before checking in instead of bouncing back and forth. BOOKED. Free hot breakfast Wednesday morning. Avoid unnecessary I-80 use if surface streets are competitive because of the Joliet reconstruction. |
7:30–8:45 PM CT |
75 min |
A relaxed sit-down dinner after the Joliet sightseeing day, with American and Mediterranean-leaning choices in the price range you wanted. Call around 6:45 PM; if the wait is running beyond roughly 20–25 minutes, Heroes West is the easy backup and can be reserved through OpenTable. |
Day 7: Wed Oct 7, 2026Joliet → Burbank → Beverly → Chicago
| Time | Stop | Time there | Notes |
|---|---|---|---|
7:30–7:50 AM CT |
20 min |
Use the hotel's included breakfast and keep it light and fast. The point is to get coffee and enough food to start the day without turning breakfast into another scheduled attraction or spoiling the fuller lunch later on. |
|
9:15 AM CT |
— |
Breakfast at the hotel and check out. Today now has one immovable deadline: you need to be settled at Willis Tower before the 6:00 PM Skydeck ticket. Check out. Avoid unnecessary I-80 shortcuts through the major Joliet construction zone. |
|
10:00–11:30 AM CT |
90 min |
The limestone prison is a major Joliet attraction in its own right and also the prison seen at the beginning of The Blues Brothers. October has no public General History guided-tour inventory, so the plan is now the self-guided visit, which lets you move through the grounds and available buildings at your own pace. TICKETS ARE PURCHASED and stored in Apple Wallet. |
|
11:45 AM–12:45 PM CT |
60 min |
Joliet's second museum gives you local history and Route 66 interpretation without duplicating the Rock & Roll Museum. One hour is enough to see the Route 66 material and keep the Chicago deadline comfortable. Current admission: $10 adult / $9 senior 60+; pay there. Current admission is $10 adult / $9 senior 60+; pay on arrival. |
|
1:00–1:40 PM CT |
40 min |
Your suggested Joliet stop fits here beautifully. It sits on old Route 66 and current weekday hours run 11 AM–6 PM, making it a quick, thematic lunch before leaving Joliet. |
|
2:25–2:50 PM CT |
25 min |
A quick dose of monster-roadside kitsch at the Halloween-themed family entertainment center. Go in, find the Dracula figure, get the photo and resist the arcade's attempt to swallow the afternoon. |
|
3:10–3:30 PM CT |
20 min |
A real stone castle rising improbably above the Beverly neighborhood. Treat it as an exterior architectural stop and be considerate of the surrounding residential streets. |
|
~4:05 PM CT |
35 min |
BOOKED. Check in, unload and PARK THE CAR. From here until Thursday afternoon, walking, CTA and rideshare are cleaner than repeatedly extracting the car from downtown traffic and parking. BOOKED. Check in, unload and park the car. Keep it parked until Thursday afternoon. |
|
4:40 PM CT |
— |
Do not schedule another attraction in this window. Leave the hotel with enough cushion for downtown traffic, walking or transit and aim to be at Skydeck around 5:00 PM, comfortably ahead of the 5:30 ticket time. |
|
5:30–6:55 PM CT |
85 min |
This is the evening anchor for Day 7. TICKETS ARE PURCHASED for 5:30 PM, giving you time to see the city in daylight, watch the approximately 6:21 PM sunset and remain into twilight as Chicago's lights begin coming on. The timing is intentionally generous so you are not racing the sun from the elevator line. |
|
7:15–7:50 PM CT |
35 min |
You do not need to stay here to enjoy the public spaces. Walk into the grand lobby, look up at the extraordinary ceiling, take in the old-hotel atmosphere and, if you like, have a quick drink or brownie-related treat at Lockwood before dinner. |
|
8:15 PM CT |
90 min |
This is the trip's one designated splurge dinner, and it is already locked in rather than left to chance on a busy Chicago night. The location opposite Millennium Park also fits the walking route naturally after Palmer House. RESERVATION BOOKED through OpenTable. |
Day 8: Thu Oct 8, 2026Chicago by foot/CTA → Hammond → Gary → Indiana Dunes → South Bend
| Time | Stop | Time there | Notes |
|---|---|---|---|
6:55 AM CT |
— |
Leave the car and luggage at the hotel and do the Chicago morning the way Chicago wants to be done: on foot and on CTA. Buy one 1-Day Ventra Ticket per person at the first convenient station; the pass covers the L and buses for 24 hours and saves you from repeatedly thinking about fares or downtown parking. |
|
7:05–7:20 AM CT |
15 min |
The historic red-brick Dearborn Station is a real Chicago landmark with a wonderfully specific television connection: it is the station referenced in the M*A*S*H episode 'Adam's Ribs' while Hawkeye tries to track down his remembered Chicago barbecue joint. The restaurant was fictional, but the station is real, making this a quick exterior stop with a great story attached. |
|
7:40–8:05 AM CT |
25 min |
Herb Alpert's bronze Spirit Totems stand outdoors in the Field Museum's Rice Native Gardens, so you can see them without buying museum admission. The tall, abstract figures give you an art stop in a completely different visual language from the roadside giants, and the early hour should make the garden feel pleasantly quiet. |
|
8:45–9:35 AM CT |
50 min |
A classic Chicago breakfast with deep Route 66 associations. Lou Mitchell's has greeted generations of travelers near the historic beginning of the Mother Road, and moving it later in the morning means you can actually enjoy a fuller breakfast instead of forcing one down immediately after waking up. |
|
9:35–9:50 AM CT |
15 min |
Walk from Lou Mitchell's to the historic Quincy station in the Loop. This is not just transportation positioning: Quincy retains the old elevated-platform atmosphere that makes the Chicago L feel unmistakably like Chicago and sets up the ride you've wanted to take for years. |
|
9:55–10:20 AM CT |
25 min |
Take a northbound Brown Line train from Quincy to Fullerton. This route gives you a genuine elevated L experience with views over downtown and the North Side instead of spending the whole ride underground. The same Ventra day pass covers the trip. |
|
10:20–10:50 AM CT |
30 min |
Walk east/southeast from Fullerton through the Lincoln Park neighborhood toward Clark and Dickens. The fiberglass cow is one of the survivors of Chicago's famous 1999 Cows on Parade public-art project, and Karen found a current Facebook post confirming it is still there. Treat it as a quick photo stop while you're already passing through the neighborhood, not a separate detour. |
|
10:50–11:10 AM CT |
20 min |
Board the northbound #22 Clark bus and let the city slide past at street level on the way to Wrigleyville. It is a good complement to the L ride and much easier than trying to move a car around Lincoln Park and Wrigley Field. Tap the Ventra pass when boarding; you do not tap again when getting off. |
|
11:10–11:30 AM CT |
20 min |
Exactly what you wanted and nothing more: walk up to the iconic red Wrigley Field marquee, get the photographs and soak up a few minutes of the neighborhood atmosphere. No stadium tour is necessary, which keeps one of baseball's most recognizable landmarks from consuming the whole morning. |
|
11:35 AM–12:10 PM CT |
35 min |
Reboard the #22 southbound and ride Clark Street back toward the Loop. Staying on the bus keeps this part of the day simple and avoids paying for taxis or fighting with parking as the itinerary transitions from North Side sights back into downtown Chicago. |
|
12:10–12:30 PM CT |
20 min |
Daley Plaza and the Picasso sculpture form one of the signature locations in the frantic finale of The Blues Brothers as Jake and Elwood race to pay the orphanage's tax bill. Seeing the real plaza adds a movie-location stop without requiring a detour because the #22 bus brings you right back into the Loop. |
|
12:40–1:00 PM CT |
20 min |
Give yourselves time to circle Anish Kapoor's mirrored sculpture instead of grabbing one hurried photograph. The reflections change with every angle, pulling in the skyline, plaza and people around you, and the Thursday timing lets you enjoy it without the pressure of Wednesday's Willis Tower reservation. |
|
1:10–1:25 PM CT |
15 min |
Photograph the traditional downtown beginning of Route 66 at Adams Street near Michigan Avenue. This is the historic starting-point moment, and seeing it on the same day as the newer Navy Pier centennial marker lets you acknowledge both the original Mother Road story and the 2026 celebration. |
|
1:40–2:15 PM CT |
35 min |
For the Route 66 Centennial, Navy Pier added a symbolic starting marker on the South Dock. Seeing it after the traditional Adams/Michigan sign gives you both versions of the Chicago starting-point story. Use this as the midday snack stop; turn it into a quick lunch only if Lou Mitchell's has worn off more than expected. |
|
2:15–2:40 PM CT |
25 min |
Finish the downtown CTA/walking loop, return to the Grant Park Hotel and retrieve the luggage and car. Once the car comes out of parking, the trip shifts back from Chicago transit mode to roadside-attraction mode for Hammond, Gary and the Indiana Dunes. |
|
~2:45 PM CT |
— |
Leave downtown using live navigation rather than a hard-coded route. The I-80/94 FlexRoad project in northwest Indiana can produce meaningful delays, so this is one place where real-time traffic should overrule the prettiest-looking route on paper. |
|
3:45–4:10 PM CT |
25 min |
Flick remains permanently displayed outside the Welcome Center with his tongue stuck to the flagpole. You are too early for the seasonal Christmas Story exhibit, but the statue itself is there year-round. |
|
4:30–4:50 PM CT |
20 min |
This is now a tightly focused collection stop, not a meal. Go in, head for the Rock Shop, pick up shirts for the collection and get back on the road; keeping it to roughly 20–25 minutes protects the late-afternoon Dunes stop. Everyone entering the casino property must be 21+ with valid government photo ID. |
|
5:20–5:50 PM CT |
30 min |
Keep this deliberately modest: the easy lakefront/riverwalk route gives you beach, Lake Michigan and dune scenery without turning a roadside-attraction vacation into a strenuous hiking day. The trail is about 0.9 mile and normally takes roughly 45 minutes. Short scenic Lake Michigan stop. No major hike. Current national-park vehicle pass is $25 and valid 7 days; no timed reservation. Current national-park vehicle pass is $25 and valid for seven days; no timed reservation is required. |
|
5:50 PM CT |
— |
Leave the lakefront and head for South Bend remembering that the clock jumps forward one hour when you return to Eastern Time. Go directly to dinner instead of checking into the hotel first; that keeps the final-night reservation from being squeezed by the time-zone change. |
|
8:30 PM ET |
75 min |
A fitting last-night dinner: relaxed, local and full-service without being fancy. You and Karen both like Irish food, and Fiddler's Hearth gives you shepherd's pie, fish and chips and other Celtic pub fare in a place with more personality than a generic chain. RESERVATION BOOKED through Toast. |
|
After dinner ET |
— |
BOOKED. Remember that you move back into Eastern Time before South Bend, so the clock jumps ahead one hour on this drive. BOOKED. Check in after dinner. Free breakfast Friday morning. |
Day 9: Fri Oct 9, 2026South Bend → Notre Dame → Wabash → Norwalk → Mentor
| Time | Stop | Time there | Notes |
|---|---|---|---|
7:00–7:25 AM ET |
25 min |
Use the hotel's included breakfast and keep it light and fast. The point is to get coffee and enough food to start the day without turning breakfast into another scheduled attraction or spoiling the fuller lunch later on. |
|
8:00–10:00 AM ET |
2 hr |
Start at the Eck Visitors Center and make a self-guided loop to the Golden Dome, Basilica of the Sacred Heart, Grotto and the Word of Life mural better known as Touchdown Jesus. Free public tours are sometimes available, but the itinerary does not depend on getting one. |
|
10:15 AM ET |
— |
This final day still has two pieces of roadside weirdness before home. |
|
11:45 AM–12:05 PM ET |
20 min |
Large metal sculptures of an Imperial Walker and Scout Walker stand outside Metal Source. They are outside the fence and visible at any time, making this an easy stop even if business hours do not cooperate. |
|
12:10–12:35 PM ET |
25 min |
Keep Wabash flexible. The default is a quick snack so the final drive does not stretch too late, but if you're ready for a proper lunch, Market Street Grill is the full-meal fallback and still keeps lunch inside the noon-to-2 window. |
|
~3:30–4:00 PM ET |
30 min |
This is the correct Norwalk stop: the new Mickey's at Benedict Avenue has developed its permanent dinosaur-themed roadside experience, with giant dinosaur figures inside the travel stop. It is open 24 hours, so timing is forgiving. Giant dinosaur figures at the current Benedict Avenue location. |
|
~6:00–6:30 PM ET |
— |
Approximate arrival. Friday traffic and how enthusiastically you investigate the dinosaurs will decide the real time. Approximate arrival; lunch choice and Friday traffic will decide the final time. |