24 Hours in Chicago
Covers 14 cities from New York, Washington and Chicago to New Orleans, Las Vegas, Montreal and Vancouver, with airport trains, day passes and Friday hotel prices.
UpdatedThis page carries dated prices, schedules or seasonal facts checked on the date above, and that window has now passed. Re-check the sources at the foot of the page before you book.
Chicago's airport ride is long but simple. The CTA Blue Line leaves from a station under O'Hare's Terminals 1, 2 and 3, runs 24 hours a day, and the CTA puts the trip to downtown at 40 to 45 minutes. Boarding at O'Hare costs $5 (£3.70), but a 1-Day Pass costs the same $5 (£3.70) and covers the O'Hare fare, so buy the pass at the machine and ride free for 24 hours.
The day is a loop of the Loop. Millennium Park and the Art Institute in the morning, a cheezborger under Michigan Avenue, the Riverwalk in the afternoon, the 360 Chicago deck as the light goes, deep dish in River North and a jazz set at 10:30 p.m. Paid entries in the plan come to $79 (£59).
At a glance
- Best for
- One great art museum, skyline views and the city's own food, finished with live jazz
- Skip it if
- You are coming in deep winter for the river, or in June on a budget
- Airport to center
- CTA Blue Line from O'Hare, about 45 minutes to the Loop, $5 (£3.70), or free on a 1-Day Pass
- One night, mid-January
- $117 (£88) for a 3-star double in the Loop; $330 (£247) on the Magnificent Mile in June
- Arrive by
- 9 a.m. at O'Hare, to be at Millennium Park by 10 a.m.
In this guide
The 24-hour plan
- 10:00 a.m.
Millennium Park and Cloud Gate
Walk east from the Blue Line to Michigan Avenue and into the park, open daily 6 a.m. to 11 p.m. and free. See the skyline bent in the steel of Cloud Gate before the crowds.
- 11:00 a.m.
Art Institute of Chicago
Across Monroe Street, doors open at 11 a.m. Give it two and a half hours: Nighthawks, A Sunday on La Grande Jatte and American Gothic are all here. Closed Tuesdays; advance tickets encouraged, not required.
- 1:45 p.m.
Lunch at the Billy Goat Tavern, lower Michigan Avenue
Walk north up Michigan Avenue to the river and take the stairs down to 430 N. Michigan Ave, lower level, for the cheezborger. Open from 6 a.m. to 2 a.m. on Fridays.
- 3:00 p.m.
Chicago Riverwalk
Back up to street level and down to the river. Walk west along the south bank under the bridges and past the towers. From March to November, swap this for the 90-minute architecture river cruise.
- 5:00 p.m.
360 Chicago observation deck
Up the Magnificent Mile to 875 N. Michigan Ave and 1,030 feet up as the light goes. Open 9 a.m. to 11 p.m.; tickets start at the online price.
- 7:30 p.m.
Deep-dish pizza at Lou Malnati's River North
Walk west into River North to 439 N. Wells Street. Deep dish takes time to bake, so order as you sit. Open until midnight on Fridays and Saturdays; reservations taken.
- 10:30 p.m.
Late set at Andy's Jazz Club
Walk east along Hubbard Street to number 11. Sets start at 6, 8:15 and 10:30 p.m.; reservations are required, each covers one show, and admission is typically about $20 a person.
- 10:00 a.m.
Chicago Cultural Center (Saturday)
Saturday morning, the Tiffany dome in Preston Bradley Hall at 78 E. Washington Street. Free, open daily 10 a.m. to 5 p.m., and a short walk from the Blue Line at Washington for the ride back to O'Hare.
The route is 5.5 miles (8.8 km) from stop to stop in a straight line; the real walk is longer.
Art Institute closed Tuesdays (and Thanksgiving, Christmas and New Year's Day); architecture river cruises run March 15 to November 22 in 2026; Andy's Jazz Club requires a reservation for every set
How the 24 hours work
Get off the Blue Line at Washington and walk east to Millennium Park, open from 6 a.m. to 11 p.m. and free. The Art Institute opens at 11 a.m. across Monroe Street; general adult admission is $32 (£24), and the museum encourages advance tickets but does not require them. After lunch at the Billy Goat Tavern below Michigan Avenue, walk the Riverwalk west, then go up the Magnificent Mile to 360 Chicago in the former John Hancock Center. Dinner is at Lou Malnati's on Wells Street, and Andy's Jazz Club on Hubbard Street is a short walk away.
Two things need booking. Andy's requires a reservation for every set, at 6, 8:15 and 10:30 p.m., and the room clears after each show. 360 Chicago sells tickets online from $27 (£20) and charges more at the gate.
The closing day to watch is Tuesday, when the Art Institute is closed. From March to November the river changes the plan: the Chicago Architecture Center River Cruise aboard First Lady runs 90 minutes from $57 (£43), and its 2026 season ends November 22. Take it in place of the Riverwalk. On a wet or frozen day, give the Art Institute the whole afternoon.
Where to stay for one night
We searched Kayak for two adults on a Friday, total price with all taxes and fees, 3 stars or better and a guest rating of 8 or more, across the Loop, River North and the Magnificent Mile:
- The Loop: the Hampton Inn Chicago Downtown/N Loop/Michigan Ave was the cheapest qualifying room on January 15, 2027, at $117 (£88), rated 8.0, a few minutes from the river and Millennium Park. The Hampton Inn Majestic in the Theatre District was $136 (£102).
- River North: the ACME Hotel was $131 (£98) in January, close to Lou Malnati's and Andy's.
- The Magnificent Mile: in June the Warwick Allerton had the cheapest qualifying room in our area at $330 (£247) on June 11, 2027. Eurostars Magnificent Mile was $136 (£102) in January and $393 (£294) in June.
June costs almost three times January here. If summer is your window, Philadelphia is the cheaper big-city night in this guide.
Getting in from the airport (and the station)
Follow the train signs to the O'Hare station on the lower level, connected to Terminals 1, 2 and 3; from Terminal 5, take the free airport shuttle train first. Every Blue Line train from O'Hare runs through downtown, with stops at Clark/Lake, Washington, Monroe and Jackson. The CTA's own chart puts the ride at about 45 minutes.
At O'Hare a single 'L' fare is $5 (£3.70), charged on entry. Everywhere else a train ride is $2.50 (£1.90). The 1-Day Pass is $5 (£3.70) and lasts 24 hours from first use, so it covers the airport ride and the rest of your day. Tap a contactless card for single rides, or buy a 1-Day Ventra Ticket at the station machine.
The CTA estimates a taxi from O'Hare to downtown at around $40 (£30) before tip, and 25 to 90 minutes depending on traffic; rideshares at around $35–$50 (£26–£37), with surges well above that. Midway, the city's second airport, is about 25 minutes from downtown on the Orange Line.
What to eat in 24 hours
- Deep-dish pizza at Lou Malnati's, 439 N. Wells Street, open until midnight on Fridays and Saturdays.
- An Italian beef at Al's #1 Italian Beef, 548 N. Wells Street, a block north of Lou's, open 10:30 a.m. to midnight Monday to Saturday. Al's has made them since 1938.
- The cheezborger at the Billy Goat Tavern, 430 N. Michigan Avenue on the lower level, open on Fridays from 6 a.m. to 2 a.m. The tavern dates to 1934.
- A drink with the 1,030-foot view at CloudBar in 360 Chicago, if you want the sunset to last.
None of these places published menu prices on their own sites when we checked, so we do not quote them. For cities where eating is the main event, see the best food cities for 24 hours.
If you only have 12 hours
Keep Millennium Park, the Art Institute and the Riverwalk, and eat at Al's or Lou's before heading back. That is about six hours in town plus 90 minutes of train. O'Hare sits about 16 miles (25 km) from the Loop in a straight line, and because the Blue Line runs all night, even a late connection works. For airport-only stopovers in Europe and Asia, see our layover guides.
What 24 hours costs
| Item | January | June |
|---|---|---|
| Hotel, one night (whole room) | $117 (£88) | $330 (£247) |
| CTA 1-Day Pass (includes the O'Hare ride in) | $5 (£3.70) | $5 (£3.70) |
| Blue Line back to O'Hare the next day | $2.50 (£1.90) | $2.50 (£1.90) |
| Art Institute, 360 Chicago, Andy's Jazz Club | $79 (£59) | $79 (£59) |
| Total | $204 (£152) | $416 (£312) |
Food is extra. 360 Chicago is priced from $27 (£20) online and Andy's admission varies by show, typically $20 (£15). In season, the architecture cruise adds $57 (£43).
Getting there from the US and the UK
O'Hare has nonstops from every other hub on our US list: JFK, Newark, Los Angeles, San Francisco, Boston, Washington Dulles, Atlanta, Miami and Dallas/Fort Worth. Chicago is too far from New York for a sensible train, so fly; see the best 24-hour trips in the US for how it compares with New York and Boston.
From the UK, American, British Airways and United fly nonstop from Heathrow, and United flies from Edinburgh. British travelers need an approved ESTA; CBP charges $10.62 (£8) to process it and $30 (£22) on approval, about $41 (£30) in all. Our entry rules guide explains how to avoid paying a third-party site more.
When to go and what is new
Winter is cheap and bitterly cold, and the river cruises stop. Late spring and early fall give you the river and walkable weather at prices between our two figures. Summer is festival season and the most expensive, as the June rate shows. From November 20 to December 24, 2026, the Christkindlmarket fills Daley Plaza at 50 W. Washington Street, open 11 a.m. to 9 p.m. on Fridays and Saturdays.
The big change is on the South Side. The Obama Presidential Center at 6001 S. Stony Island Avenue is open, with museum tickets at $30 (£22) for adults and availability updated on the second Wednesday of each month. It is too far from the Loop for this plan, and tickets are scarce, so treat it as the reason for a second night.
Chicago’s Snack Score
How well Chicago works for 24 hours and one night: six factors, scored 0 to 10 the same way for all 45 cities. How we score
- Sights in a dayEditors · 30%8.0
- FoodEditors · 15%8.0
- After darkEditors · 10%8.0
- Compact routeData · 15%7.9
- Airport to centerData · 15%6.4
- One-night costData · 15%3.7
The numbers behind the score
- Airport to center
- 45 min from Chicago O'Hare International Airport: CTA Blue Line 'L' train from the O'Hare station (lower level, connected to Terminals 1, 2 and 3) to the Loop, 24 hours a day, $5 (£3.70)
- One night, Friday
- $117 (£88) on January 15, 2027 · $330 (£247) on June 11, 2027 (The Loop (January: Hampton Inn Chicago Downtown/N Loop/Michigan Ave, 3-star, 8.0) and the Magnificent Mile (June: Warwick Allerton Chicago, 4-star, 8.1))
- Day ticket
- CTA 1-Day Pass (24 hours from first use, CTA and Pace; covers boarding at O'Hare): $5 (£3.70)
- 24 hours, per person
- $127 (£95): half the average room, the airport ride both ways and a day ticket (entries extra)
- Nonstop from the US
- JFK, EWR, LAX, SFO, BOS, IAD, ATL, MIA, DFW
- Nonstop from the UK
- LHR, EDI
Hotel prices: Cheapest 3-star-or-better double, 1 night (Friday), 2 adults, stay total including all taxes and fees, guest rating 8+, Kayak city search and Near North Side area search sorted by price, each result's neighborhood and property type checked (a motel was excluded). Kayak, checked 2026-10-21.
Weather month by month
Best months for walking around by our weather score: May, June, September. Daytime highs and lows, rain days (1 mm or more) and sunshine hours are 2016–2025 averages for Chicago (Open-Meteo historical weather archive).
| Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec | |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| High °F | 33 | 37 | 47 | 56 | 67 | 79 | 82 | 80 | 76 | 63 | 49 | 39 |
| High °C | 0 | 3 | 8 | 14 | 19 | 26 | 28 | 27 | 24 | 17 | 9 | 4 |
| Low °F | 20 | 22 | 32 | 40 | 51 | 62 | 67 | 67 | 62 | 49 | 36 | 26 |
| Rain days | 10 | 9 | 11 | 14 | 13 | 12 | 12 | 11 | 10 | 12 | 8 | 9 |
| Sun (hours) | 5 | 7 | 8 | 9 | 10 | 12 | 12 | 12 | 10 | 8 | 6 | 5 |
| Weather score | 3.0 | 3.7 | 5.2 | 7.0 | 8.5 | 8.7 | 7.8 | 8.4 | 9.1 | 8.4 | 5.7 | 3.1 |
Where Chicago ranks
Tickets and tours you can book
Chicago River: 1.5-Hour Guided Architecture Cruise
Runs year-round with an open top deck and a climate-controlled lower deck; drinks and snacks are sold on board and you may bring your own non-alcoholic drinks. Check in with a dock employee at 400 N Michigan Ave for the boarding point.
Rating as shown on GetYourGuide
Chicago By Night River and Lake Cruise
Taxes, fees and gratuities are included; drinks and snacks are sold on board. Board at 112 E Wacker Dr: take the stairs down from the northeast corner of Michigan and Wacker to the Riverwalk box office. It runs in all weather, so bring a layer after September.
Rating as shown on Viator
Chicago: Gangsters and Food Tasting Walking Tour
Three tastings plus water or a soft drink are included; alcohol and tips are not. Meets outside Hoyt's at the Royal Sonesta Hotel on the Chicago River. Short and central, so it fits between the river cruise and dinner.
Rating as shown on GetYourGuide
Booking through these links supports this site at no cost to you. Prices move by date, so we do not print them here; the official prices we checked are in the page above.
Frequently asked questions
How long does the Blue Line take from O'Hare to downtown Chicago?
The CTA puts the normal travel time at 40 to 45 minutes. Trains run 24 hours a day, every day, and every train from O'Hare goes through downtown.
How much is the train from O'Hare?
A ride starting at O'Hare costs $5 (£3.70). A 1-Day Pass also costs $5 (£3.70), lasts 24 hours from first use and covers the O'Hare fare, so it is the better buy if you ride again that day.
What day is the Art Institute of Chicago closed?
Tuesdays, plus Thanksgiving, Christmas and New Year's Day. It opens at 11 a.m. and closes at 5 p.m., except Thursdays, when it stays open until 8 p.m. General adult admission is $32 (£24).
When do Chicago architecture boat tours run?
The Chicago Architecture Center River Cruise aboard First Lady runs from March to November; its 2026 season is March 15 to November 22. The cruise lasts 90 minutes and tickets start at $57 (£43).
Is one day enough in Chicago?
For the Loop, the Art Institute, the river and one deep-dish dinner, yes. The Museum Campus, Wrigley Field and the Obama Presidential Center need a second day.
Further reading
Official sources
- CTA: Service to and from the airports (official) – Blue Line 24 hours, O'Hare to downtown 40 to 45 minutes, station connected to Terminals 1 to 3; taxi around $40 (£30) and rideshare $35–$50 (£26–£37) estimates; checked October 21, 2026
- CTA: Fares (official) – 'L' fare $2.50 (£1.90), O'Hare boarding fare $5 (£3.70), 1-Day Pass $5 (£3.70) for 24 hours, passes cover O'Hare boarding; checked October 21, 2026
- City of Chicago: Millennium Park (official) – Open daily 6 a.m. to 11 p.m., free; checked October 21, 2026
- City of Chicago: Chicago Cultural Center (official) – 78 E. Washington St, open daily 10 a.m. to 5 p.m., free, Tiffany dome; checked October 21, 2026
- Art Institute of Chicago: Visit (official) – Hours, closed Tuesdays, adult general admission $32 (£24), advance tickets encouraged not required; checked October 21, 2026
- Billy Goat Tavern: Michigan Avenue (official) – 430 N. Michigan Ave lower level, Friday 6 a.m. to 2 a.m.; checked October 21, 2026
- 360 Chicago (official) – Open 9 a.m. to 11 p.m., 1,030 feet up, tickets from $27 (£20) online; checked October 21, 2026
- Lou Malnati's: Locations (official) – River North, 439 N. Wells St, open to midnight Friday and Saturday; checked October 21, 2026
- Al's #1 Italian Beef: River North (official) – 548 N. Wells St, Monday to Saturday 10:30 a.m. to midnight; checked October 21, 2026
- Andy's Jazz Club (official) – 11 E. Hubbard St, sets at 6, 8:15 and 10:30 p.m., reservations required, admission typically $20 (£15); checked October 21, 2026
- First Lady Cruises: Chicago Architecture Center River Cruise (official) – 90 minutes, from $57 (£43), 2026 season March 15 to November 22; checked October 21, 2026
- Christkindlmarket Chicago at Daley Plaza (official) – November 20 to December 24, 2026, Friday and Saturday 11 a.m. to 9 p.m.; checked October 21, 2026
- Obama Presidential Center: Museum tickets (official) – Adult $30 (£22), availability updated the second Wednesday of each month; 6001 S. Stony Island Ave; checked October 21, 2026
- Kayak hotel search, Chicago and Near North Side – Stay totals with all taxes and fees for January 15 and June 11, 2027, 3-star+, rating 8+; checked October 21, 2026
- U.S. Customs and Border Protection: ESTA FAQ (official) – $10.62 (£8) processing fee plus $30 (£22) on approval; checked October 21, 2026
- Wikipedia: O'Hare International Airport, Airlines and destinations – Nonstop routes from US and UK hubs; checked October 21, 2026
