Roadside Attractions + Route 66
Mentor → Indianapolis → Illinois Route 66 → Chicago → South Bend → Mentor · October 1–9, 2026
Wednesday sunset anchor: Chicago sunset on October 7, 2026 is about 6:21 PM CDT. Your requested 6:00 PM Skydeck ticket stays in the plan. Do not add another stop between Chicago hotel check-in and Willis Tower; aim to be at Skydeck around 5:25–5:30.
Indiana US 40 rule: Turn on Avoid Highways for the Indiana US 40 legs, but also inspect the route before starting. The route buttons deliberately use Richmond, Greenfield, Plainfield and Brazil as control points. Turn Avoid Highways back off when the US 40 leg is over.
Time-zone heads-up: On Saturday you gain an hour when you cross from Indiana into Illinois (Eastern → Central). On Thursday evening you lose that hour again traveling from northwest Indiana toward South Bend (Central → Eastern). Times below are labeled ET or CT where the change matters.
Booked hotels
- Thu Oct 1, 2026: Homewood Suites by Hilton Indianapolis Downtown IUPUI — 414 W Vermont St, Indianapolis, IN 46202
- Sat Oct 3, 2026: Eighteen-Ninety Sleepover — 14 South Central Avenue, Casey, IL 62420
- Sun Oct 4, 2026: Spark by Hilton Springfield Southwest — 3446 Freedom Dr., Springfield, IL 62704
- Mon Oct 5, 2026: Quality Inn Pontiac — 1823 West Reynolds Street, Pontiac, IL 61764
- Tue Oct 6, 2026: Fairfield by Marriott Inn & Suites Joliet — 3239 Norman Avenue, Joliet, IL 60435
- Wed Oct 7, 2026: Grant Park Hotel — 1100 S Michigan Avenue, Chicago, IL 60605
- Thu Oct 8, 2026: Wingate by Wyndham South Bend/Notre Dame — 52890 SR 933, South Bend, IN 46637
Google Maps route buttons
Day 1A: Mentor → Springfield, OhioOpen route in Google MapsDay 1B: Springfield → Indianapolis via US 40 controlsOpen route in Google MapsDay 2A: Indianapolis morningOpen route in Google MapsDay 2B: Indianapolis afternoonOpen route in Google MapsDay 3A: Indianapolis → Terre Haute on US 40Open route in Google MapsDay 3B: Terre Haute → CaseyOpen route in Google MapsDay 4: Casey → Champaign → Vandalia → SpringfieldOpen route in Google MapsDay 5: Springfield → Atlanta → PontiacOpen route in Google MapsDay 6A: Pontiac Route 66 corridor → JolietOpen route in Google MapsDay 6B: Joliet afternoon → hotelOpen route in Google MapsDay 7A: Joliet → Chicago hotelOpen route in Google MapsDay 7B: Chicago sunset eveningOpen route in Google MapsDay 8A: Chicago sightseeingOpen route in Google MapsDay 8B: Chicago → Hammond → Dunes → South BendOpen route in Google MapsDay 9: Notre Dame → Wabash → Norwalk → MentorOpen route in Google Maps
Day-by-day schedule
Day 1: Thu Oct 1, 2026
| Time | Stop | Time there | Notes |
|---|---|---|---|
| 6:30 AM ET | Depart Mentor Mentor, OH Map | — | Required Early departure is intentional. The first two Ohio stops are arranged to avoid the Newark/Frazeysburg backtrack from the earlier version. |
| 8:50 AM ET | Giant Apple Basket 5563 Raiders Rd, Frazeysburg, OH 43822 Map | 25 min | Must 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. Source / details |
| 9:45 AM ET | Longaberger Big Basket 1500 E Main St, Newark, OH 43055 Map | 30 min | Must 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. Source / details |
| 11:45 AM ET | Lunch in Springfield, Ohio 14 E Main St, Springfield, OH 45502 Map | 55 min | Suggested Casa Centro remains a convenient downtown suggestion, but this meal is deliberately flexible if the morning stops run long. Source / details |
| 12:50 PM ET | Hartman Rock Garden 1905 Russell Ave, Springfield, OH 45506 Map | 45 min | Must 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. Source / details |
| 2:20 PM ET | Vandalia Art Park 256 E Alkaline Springs Rd, Vandalia, OH 45377 Map | 45 min | Must 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. Source / details |
| Route control ET | US 40 through Richmond Richmond, IN Map | — | Required Turn on Google Maps' Avoid Highways option when you reach Indiana, but still inspect the blue route and make sure it stays on US 40. Richmond is included as a control point to keep Maps away from I-70. Source / details |
| Route control ET | US 40 through Greenfield Greenfield, IN Map | — | Required Continue west on US 40. Keeping Greenfield as a waypoint gives Maps another reason not to sneak you onto I-70. Source / details |
| 5:20 PM ET | Big Pink Elephant 308 W Broadway St, Fortville, IN 46040 Map | 15 min | Must A wonderfully shameless roadside photo stop: a large pink elephant outside Elite Beverages. This is the Fortville elephant, not Shipshewana. Source / details |
| 6:10 PM ET | Homewood Suites by Hilton Indianapolis Downtown IUPUI 414 W Vermont St, Indianapolis, IN 46202 Map | — | Overnight BOOKED for October 1 and 2. The downtown/IUPUI location works well for the Canal Walk and keeps the rest of Friday's Indianapolis circuit compact. Source / details |
| 7:15 PM ET | Dinner: Slippery Noodle Inn 372 S Meridian St, Indianapolis, IN 46225 Map | 75 min | Suggested A casual first-night choice with Indianapolis music history and atmosphere. Save the more expensive Indianapolis dinner for Friday if you want your splurge night here. Source / details |
Day 2: Fri Oct 2, 2026
| Time | Stop | Time there | Notes |
|---|---|---|---|
| 7:45 AM ET | Indianapolis Canal Walk 801 W Washington St, Indianapolis, IN 46204 Map | 45 min | Must 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. Source / details |
| 9:00 AM ET | Indianapolis Motor Speedway Museum 4750 W 16th St, Indianapolis, IN 46222 Map | 2 hr 30 min | Must This is one of the trip's true destination attractions, not a quick roadside stop. Give the renovated museum at least two and a half hours for the cars, racing history and gift shop. Source / details |
| 11:45 AM ET | Lunch at Mug-n-Bun 5211 W 10th St, Speedway, IN 46224 Map | 60 min | Suggested 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. Source / details |
| 1:15 PM ET | The Pyramids 3500 DePauw Blvd, Indianapolis, IN 46268 Map | 15 min | Must Three enormous office buildings designed as stepped pyramids. This one is intentionally short: park where permitted, get the geometric photos, and move on. Source / details |
| 1:45 PM ET | Holliday Park and the Ruins 6363 Spring Mill Rd, Indianapolis, IN 46260 Map | 60 min | Must 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. Source / details |
| 3:00 PM ET | Twisted House at Indy Art Center 820 E 67th St, Indianapolis, IN 46220 Map | 30 min | Must 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. Source / details |
| 3:45 PM ET | Benjamin Harrison gravesite at Crown Hill 700 W 38th St, Indianapolis, IN 46208 Map | 45 min | Must 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. Source / details |
| 4:50 PM ET | Elvis final-concert plaque 360 Market Square, Indianapolis, IN 46204 Map | 15 min | Must A compact music-history stop at the former Market Square Arena site, commemorating Elvis Presley's final concert on June 26, 1977. Source / details |
| 5:10 PM ET | Monument Circle and Soldiers & Sailors Monument 1 Monument Cir, Indianapolis, IN 46204 Map | 45 min | Must Walk the Circle and see the monument from street level. The observation level is currently closed for repairs, so do not build the day around going up; recheck shortly before the trip in case that changes. Source / details |
| 6:30 PM ET | Indianapolis nicer-dinner choice Downtown Indianapolis, IN Map | 1 hr 45 min | Suggested This is the best night for your Indianapolis splurge. FIRST CHOICE: St. Elmo Steak House, the historic downtown institution. ALTERNATIVE: Vida, a modern fine-dining restaurant with tasting-menu options. Reserve whichever one you choose. Source / details |
| After dinner ET | Shining a Light at Monument Circle 1 Monument Cir, Indianapolis, IN 46204 Map | 20 min | Optional If the projection program is operating that evening, loop back after dinner. It is an easy optional flourish because you are already downtown. Source / details |
| Restaurant alternate ET | Vida 601 E New York St, Indianapolis, IN 46202 Map | — | Optional Your second Indianapolis splurge candidate. Vida is open Tuesday through Saturday evenings and is a more contemporary, tasting-menu-oriented choice than St. Elmo. Source / details |
Day 3: Sat Oct 3, 2026
| Time | Stop | Time there | Notes |
|---|---|---|---|
| 7:30 AM ET | Depart Indianapolis 414 W Vermont St, Indianapolis, IN 46202 Map | — | Required Breakfast at the hotel, check out, and start your principal US 40 day. Keep I-70 off the menu. |
| 8:15 AM ET | Grave in the Road 6844 E 400 S, Franklin, IN 46131 Map | 15 min | Must 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. Source / details |
| 8:45 AM ET | Big John Rocking Chair 4108 US-31 S, Franklin, IN 46131 Map | 15 min | Must A giant rocking chair outside Long's Furniture. Exactly the kind of ten-minute photograph that keeps a roadside trip delightfully peculiar. Source / details |
| Route control ET | US 40 through Plainfield Plainfield, IN Map | — | Required Turn on Avoid Highways and verify US 40 before starting this leg. Plainfield is a routing control point, not an attraction stop. Source / details |
| Route control ET | US 40 through Brazil Brazil, IN Map | — | Required Stay on the historic National Road west toward Terre Haute. Do not accept an I-70 reroute. Source / details |
| 11:15 AM ET | Terre Haute murals and lunch Downtown Terre Haute, IN Map | 1 hr 45 min | Must 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. Source / details |
| 12:30 PM CT | World's Largest Gavel 501 Archer Ave, Marshall, IL 62441 Map | 20 min | Must 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. Source / details |
| 1:00 PM CT | 1918 Brick National Road section Marshall, IL 62441 Map | 25 min | Must 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. Source / details |
| 1:50 PM CT | Casey giant-attraction circuit Downtown Casey, IL 62420 Map | 3 hr 10 min | Must 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. Source / details |
| 5:05 PM CT | Eighteen-Ninety Sleepover 14 South Central Avenue, Casey, IL 62420 Map | 30 min | Overnight 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. Source / details |
| 5:45 PM CT | Dinner at Richards Farm 607 NE 13th St, Casey, IL 62420 Map | 75 min | Suggested 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. Source / details |
Day 4: Sun Oct 4, 2026
| Time | Stop | Time there | Notes |
|---|---|---|---|
| 6:45 AM CT | Optional final Casey photos Downtown Casey, IL 62420 Map | 30 min | Optional Use the quiet morning only for giants you missed or want in softer light. Otherwise enjoy breakfast and leave a little later. Source / details |
| 7:30 AM CT | Depart Casey 14 South Central Avenue, Casey, IL 62420 Map | — | Required Today's clock is built around the 1:30 PM Dana-Thomas House tour, so that reservation becomes the anchor. |
| 8:45 AM CT | Humpty Dumpty 106 N Walnut St, Champaign, IL 61820 Map | 15 min | Must A giant Humpty Dumpty perched outside the Esquire Lounge. This is a pure hop-out-and-grin photo stop before turning back southwest. Source / details |
| 10:30 AM CT | Kaskaskia Dragon 2024 Progress West Dr, Vandalia, IL 62471 Map | 25 min | Must The fire-breathing metal dragon is in Vandalia, Illinois. Viewing is free; the flame effect requires a token, so think of actual fire as a bonus rather than a promise on a Sunday morning. Source / details |
| 12:00 PM CT | Lunch in Springfield Springfield, IL Map | 50 min | Suggested Keep this meal fairly quick because the Dana-Thomas tour is fixed. Obed & Isaac's is a good central option if timing works; otherwise choose something close to the house. Source / details |
| 1:30 PM CT | Dana-Thomas House 301 E Lawrence Ave, Springfield, IL 62703 Map | 60 min | Must Your Frank Lloyd Wright stop. This is not just a drive-by: the remarkable 1902 house contains one of the largest intact collections of Wright-designed art glass and furniture. Reserve the 1:30 PM tour in advance. Source / details |
| 3:00 PM CT | Lincoln Tomb 1500 Monument Ave, Springfield, IL 62702 Map | 45 min | Must 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. Source / details |
| 4:15 PM CT | Auburn Brick Road Snell Rd and Curran Rd, Auburn, IL 62615 Map | 45 min | Must 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. Source / details |
| 5:20 PM CT | Spark by Hilton Springfield Southwest 3446 Freedom Dr., Springfield, IL 62704 Map | 25 min | Overnight BOOKED. Check in before dinner; the southwest location is convenient for the Auburn return and the evening Motorheads run. Source / details |
| 5:50 PM CT | Dinner at Route 66 Motorheads Bar & Grill 600 Toronto Rd, Springfield, IL 62711 Map | 1 hr 25 min | Must 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. Source / details |
| 7:35 PM CT | Illinois State Fairgrounds Route 66 Experience 801 E Sangamon Ave, Springfield, IL 62702 Map | 45 min | Suggested A walk-through miniature tour of Illinois Route 66 with signs, replicas and neon. After dark is exactly when the neon earns its keep. Source / details |
Day 5: Mon Oct 5, 2026
| Time | Stop | Time there | Notes |
|---|---|---|---|
| 7:15 AM CT | Breakfast at Charlie Parker's Diner 700 North St, Springfield, IL 62704 Map | 55 min | Suggested A much better home for this suggestion than trying to wedge it into lunch. The funky diner is known for oversized breakfasts and was featured on Diners, Drive-Ins and Dives; current hours are 7 AM–2 PM. Source / details |
| 8:50 AM CT | Lincoln Home Visitor Center 426 S 7th St, Springfield, IL 62701 Map | 20 min | Required 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. Source / details |
| 9:15 AM CT | Lincoln Home and neighborhood 413 S 8th St, Springfield, IL 62701 Map | 45 min | Must 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. Source / details |
| 10:15 AM CT | Abraham Lincoln Presidential Library and Museum 212 N 6th St, Springfield, IL 62701 Map | 2 hr 30 min | Must Another major attraction that deserves breathing room. The museum mixes original artifacts with immersive theatrical exhibits, so two and a half hours is a reasonable minimum rather than an extravagance. Source / details |
| 1:00 PM CT | Lunch at Cozy Dog Drive In 2935 S 6th St, Springfield, IL 62703 Map | 50 min | Suggested 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. Source / details |
| 2:40 PM CT | American Giants Museum 100 NE Arch St, Atlanta, IL 61723 Map | 55 min | Must 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. Source / details |
| 3:35 PM CT | Bunyon Giant and downtown Atlanta 103 SW Arch St, Atlanta, IL 61723 Map | 35 min | Must 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. Source / details |
| 5:20 PM CT | Pontiac Route 66 Centennial Plaza, murals and giant shield 110 W Howard St, Pontiac, IL 61764 Map | 75 min | Must 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. Source / details |
| 6:40 PM CT | Quality Inn Pontiac 1823 West Reynolds Street, Pontiac, IL 61764 Map | 25 min | Overnight BOOKED. Check in after the downtown walk, then choose dinner based on how ambitious you still feel. Source / details |
| 7:15 PM CT | Dinner in Pontiac Pontiac, IL Map | 75 min | Suggested Old Log Cabin is REMOVED from dinner because it closes at 2 PM. Route 66 RoadHouse is the more thematic possibility if its Monday October dinner hours are confirmed; Endzone Bar & Grill is a dependable later-hours fallback. Source / details |
Day 6: Tue Oct 6, 2026
| Time | Stop | Time there | Notes |
|---|---|---|---|
| 9:00 AM CT | Route 66 Association Hall of Fame & Museum 110 W Howard St, Pontiac, IL 61764 Map | 1 hr 15 min | Must 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. Source / details |
| 10:35 AM CT | Standard Oil Gas Station 400 S West St, Odell, IL 60460 Map | 25 min | Must 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. Source / details |
| 11:20 AM CT | Ambler's Texaco Station 417 W Waupansie St, Dwight, IL 60420 Map | 25 min | Must 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. Source / details |
| 11:50 AM CT | Lunch at Old Route 66 Family Restaurant 105 S Old Route 66, Dwight, IL 60420 Map | 55 min | Suggested 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. Source / details |
| 1:05 PM CT | Two-Cell Jail 400 E Mazon St, Gardner, IL 60424 Map | 20 min | Suggested 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. Source / details |
| 1:40 PM CT | Polk-a-Dot Drive In 222 N Front St, Braidwood, IL 60408 Map | 30 min | Must 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. Source / details |
| 2:30 PM CT | Gemini Giant 201 Bridge St, Wilmington, IL 60481 Map | 35 min | Must 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. Source / details |
| 3:40 PM CT | Illinois Rock & Roll Museum on Route 66 9 W Cass St, Joliet, IL 60432 Map | 60 min | Must 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. Source / details |
| 4:45 PM CT | Rialto Square Theatre marquee 102 N Chicago St, Joliet, IL 60432 Map | 20 min | Suggested The ornate 1926 theater is one of downtown Joliet's visual showpieces. No tour needed; photograph the façade and marquee, then keep moving. Source / details |
| 5:15 PM CT | Rich & Creamy / Route 66 Park / Blues Brothers 920 N Broadway St, Joliet, IL 60435 Map | 30 min | Must 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. Source / details |
| 5:55 PM CT | Jacob Henry Mansion exterior 20 S Eastern Ave, Joliet, IL 60433 Map | 20 min | Suggested A quick look at an elaborate 1873 Renaissance Revival mansion. This is intentionally an exterior bonus, not another tour. Source / details |
| 6:40 PM CT | Fairfield by Marriott Inn & Suites Joliet 3239 Norman Avenue, Joliet, IL 60435 Map | — | Overnight BOOKED. The hotel is outside downtown, so finish the downtown attractions before checking in instead of bouncing back and forth. Source / details |
| 7:15 PM CT | Dinner in Joliet Joliet, IL Map | 75 min | Flexible Keep this one flexible. You have another Joliet restaurant planned for Wednesday lunch, so tonight can simply be whatever looks good near the hotel after a long Route 66 day. Source / details |
Day 7: Wed Oct 7, 2026
| Time | Stop | Time there | Notes |
|---|---|---|---|
| 9:15 AM CT | Depart Fairfield Joliet 3239 Norman Avenue, Joliet, IL 60435 Map | — | Required 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. |
| 10:00 AM CT | Old Joliet Prison 1125 Collins St, Joliet, IL 60432 Map | 1 hr 30 min | Must The limestone prison is a major Joliet attraction in its own right and also the prison from the opening of The Blues Brothers. Reserve a tour if the October schedule offers one; otherwise allow time for the exterior grounds and interpretive material. Source / details |
| 11:45 AM CT | Joliet Area Historical Museum / Route 66 Welcome Center 204 N Ottawa St, Joliet, IL 60432 Map | 60 min | Must 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. Source / details |
| 1:00 PM CT | Lunch at Doggy Dogs 1601 S Chicago St, Joliet, IL 60436 Map | 40 min | Suggested 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. Source / details |
| 2:25 PM CT | Dracula at Haunted Trails 7759 S Harlem Ave, Burbank, IL 60459 Map | 25 min | Must 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. Source / details |
| 3:10 PM CT | Givins Beverly Castle 10244 S Longwood Dr, Chicago, IL 60643 Map | 20 min | Must 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. Source / details |
| 4:05 PM CT | Grant Park Hotel 1100 S Michigan Avenue, Chicago, IL 60605 Map | 35 min | Overnight 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. Source / details |
| 5:10 PM CT | Leave hotel for Willis Tower 1100 S Michigan Ave, Chicago, IL 60605 Map | — | Required Do not schedule another attraction in this window. The goal is to be physically at Skydeck around 5:25–5:30, leaving a cushion for downtown movement, security and elevators. Source / details |
| 6:00 PM CT | Skydeck Chicago at Willis Tower — SUNSET 233 S Wacker Dr, Chicago, IL 60606 Map | 1 hr 15 min | Must This is the new anchor for Day 7. Sunset on October 7, 2026 is about 6:21 PM CDT, so a 6:00 ticket gives only about 21 minutes before sunset. Skydeck advises arriving 30–45 minutes before sunset; if a 5:30 ticket is ever acceptable to you it provides more insurance, but this itinerary protects your requested 6:00 PM ticket. Stay through dusk as the city lights come on. Source / details |
| 7:35 PM CT | Palmer House lobby 17 E Monroe St, Chicago, IL 60603 Map | 35 min | Must 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. Source / details |
| 8:20 PM CT | Chicago nicer-dinner choice Downtown Chicago, IL Map | 1 hr 30 min | Suggested Best geographic choice after Palmer House: ACANTO at 18 S Michigan, an Italian restaurant and wine bar across from Millennium Park. Bigger splurge alternative: GIBSONS ITALIA at 233 N Canal, a modern Italian steakhouse with river and skyline views. Either can be your one Chicago 'spend a little more' meal. Source / details |
| Restaurant alternate CT | Gibsons Italia 233 N Canal St, Chicago, IL 60606 Map | — | Optional The more dramatic special-occasion option: steaks, Italian dishes and excellent city/river views. It is less convenient than Acanto after Palmer House, but stronger if the dinner itself is meant to be an event. Source / details |
Day 8: Thu Oct 8, 2026
| Time | Stop | Time there | Notes |
|---|---|---|---|
| 7:30 AM CT | Herb Alpert Spirit Totems — Rice Native Gardens 1400 S DuSable Lake Shore Dr, Chicago, IL 60605 Map | 35 min | Must Good news restored: Herb Alpert's bronze Spirit Totems are currently listed by the Field Museum as features of its Rice Native Gardens. The gardens are outside, free and open year-round, so you can see the sculptures without buying museum admission. Source / details |
| 8:10 AM CT | Return to Grant Park Hotel / leave luggage 1100 S Michigan Ave, Chicago, IL 60605 Map | 15 min | Required Check out if convenient but leave bags with the hotel and keep the car parked. You'll retrieve everything after the downtown sightseeing loop. Source / details |
| 8:20 AM CT | CTA to Wrigley Field Roosevelt station to Addison station, Chicago, IL Map | — | Required Use the Red Line rather than driving north and paying to park for a twenty-minute photograph. Wrigley itself encourages public transit. Source / details |
| 8:55 AM CT | Wrigley Field red marquee sign 1060 W Addison St, Chicago, IL 60613 Map | 20 min | Must Exactly what you want and nothing more: walk up to the iconic red Wrigley Field marquee, get the photographs, absorb a few minutes of Wrigleyville, and head back downtown. No stadium tour and no dependence on the Cubs' postseason fortunes. Source / details |
| 9:50 AM CT | Cloud Gate — The Bean 201 E Randolph St, Chicago, IL 60602 Map | 30 min | Must Move the Bean from Wednesday night to Thursday. In morning light you'll have time to circle Anish Kapoor's mirrored sculpture, photograph the skyline reflections and avoid rushing from the hotel to Willis Tower the night before. Source / details |
| 10:30 AM CT | Traditional Route 66 Begin sign 78-98 E Adams St, Chicago, IL 60603 Map | 20 min | Must Photograph the traditional downtown beginning of Route 66 at Adams Street near Michigan Avenue. This is the historic starting-point moment before you also visit the new centennial marker at Navy Pier. Source / details |
| 11:10 AM CT | Navy Pier Route 66 Centennial starting point 600 E Grand Ave, Chicago, IL 60611 Map | 60 min | Must For the centennial, Navy Pier has added a symbolic Route 66 starting point on the South Dock. Seeing both this marker and Adams/Michigan lets you acknowledge the new centennial celebration without pretending the historic route suddenly began on the pier. Source / details |
| 12:25 PM CT | Lunch at Lou Mitchell's 565 W Jackson Blvd, Chicago, IL 60661 Map | 55 min | Suggested A perfect farewell-to-Chicago lunch: the classic diner has greeted generations of travelers near the beginning of Route 66. Current Thursday hours run early morning to 2 PM, so this works much better as lunch than dinner. Source / details |
| 1:30 PM CT | Retrieve car and luggage / depart Chicago 1100 S Michigan Ave, Chicago, IL 60605 Map | — | Required Get the car, point it southeast, and leave downtown. This departure is intentionally earlier than the previous version because Wrigley has moved to this morning. |
| 2:35 PM CT | Indiana Welcome Center — Flick statue 7770 Corinne Dr, Hammond, IN 46323 Map | 30 min | Must 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. Source / details |
| 3:45 PM CT | Indiana Dunes National Park — Portage Lakefront & Riverwalk 100 Riverwalk Rd, Portage, IN 46368 Map | 1 hr 15 min | Must 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. Source / details |
| 7:00 PM ET | Wingate by Wyndham South Bend/Notre Dame 52890 SR 933, South Bend, IN 46637 Map | — | Overnight BOOKED. Remember that you move back into Eastern Time before South Bend, so the clock jumps ahead one hour on this drive. Source / details |
| 7:30 PM ET | Dinner in South Bend / Notre Dame area South Bend, IN Map | 75 min | Flexible Rohr's on the Notre Dame campus remains a good choice if you want an early peek at campus. Otherwise keep dinner convenient near the hotel after the time-zone change and lakefront stop. Source / details |
Day 9: Fri Oct 9, 2026
| Time | Stop | Time there | Notes |
|---|---|---|---|
| 8:00 AM ET | Notre Dame campus 100 Eck Center, Notre Dame, IN 46556 Map | 2 hr | Must 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. Source / details |
| 10:15 AM ET | Depart Notre Dame Notre Dame, IN Map | — | Required This final day still has two pieces of roadside weirdness before home. |
| 11:45 AM ET | Star Wars Imperial Walkers 1733 S Wabash St, Wabash, IN 46992 Map | 20 min | Must 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. Source / details |
| 12:15 PM ET | Lunch in Wabash Wabash, IN Map | 50 min | Flexible Keep lunch fairly quick so Norwalk and the drive home stay comfortable. Pick locally based on what sounds good that day. Source / details |
| 3:30 PM ET | Mickey's Dino-World Adventure 251 Benedict Ave, Norwalk, OH 44857 Map | 30 min | Must 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. Source / details |
| 6:00 PM ET | Return to Mentor Mentor, OH Map | — | Required Approximate arrival. Friday traffic and how enthusiastically you investigate the dinosaurs will decide the real time. |