AllTrails
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Chicago Travel Guide
The best US city to visit without a car
- Illinois
- August 2026
- The best US city to visit without a car
Why go to Chicago
Chicago is dense, walkable, and served by more rail than almost any American city, which makes it the rare big trip where renting a car is usually the wrong call.
Two airports, a national Amtrak hub at Union Station, and a downtown you can cross on foot in 30 minutes mean your transportation decision here is mostly about how you arrive, not how you get around.
How to get there
Train
Union Station is the Midwest rail hub, with corridor service from Milwaukee, St. Louis, and Detroit.
Flights
O'Hare for connections and international routes, Midway for cheaper domestic point-to-point.
Driving
Doable, but expect $45 to $75 per night for downtown parking.
Rental Car
Only worth it if you are day-tripping to the dunes or Wisconsin.
Getting around
- The L covers nearly every neighborhood a visitor wants; the Blue Line reaches O'Hare in about 45 minutes.
- Walk the Loop and River North. Cabs and rideshare are only worth it late at night.
- Divvy bikes along the lakefront trail are the single best way to see the skyline.
What to do in Chicago
2 to 3 hours
Art Institute of Chicago
One of the strongest collections in the country, and two hours is enough.
90 minutes
River Architecture Cruise
The single best orientation to the city, from the water.
Half day
Lakefront Trail by Bike
18 miles of car-free shoreline with skyline views the whole way.
Full day
Indiana Dunes Day Trip
Reachable by train, with real dune climbs at the end.
3 hours
Cubs at Wrigley Field
Worth planning a trip around between April and September.
3 hours
Pilsen Food Walk
Taquerias and murals in one long, cheap afternoon.
Outdoor options nearby
Easy
Chicago Lakefront Trail
18 car-free miles along Lake Michigan, the best urban ride in the Midwest.
Easy
Indiana Dunes Camping
Dunewood Campground puts a national park 90 minutes from the Loop.
A workable plan
- Art Institute, then walk Michigan Avenue
- Architecture boat tour on the river
- Dinner in West Loop
- Divvy the lakefront trail north
- Lincoln Park Zoo and conservatory
- Cubs or Sox game if in season
- Pilsen murals and taquerias
- Indiana Dunes day trip by South Shore Line
- Late blues set in Bronzeville
Chicago questions
How many days do you need in Chicago?
Two full days covers the essentials and three lets you add a day trip or an outdoor morning without rushing.
What is the best way to get around Chicago?
Check the getting-around notes above first: in some cities transit and walking beat a rental car outright, and in others a car is the only practical option.
Travel services for Chicago
The tools and providers that fit the way this trip actually works.
Hotels
Best used as a price check and a way to filter for genuinely refundable rates rather than as your only lodging search.
Varies by market; always compare against the hotel's direct rate.
Tours & Attractions
Strongest for skip-the-line attraction tickets and half-day tours you would otherwise queue for.
Attraction tickets from about $25; half-day tours from about $70.
