Chicago, ILBy ArrivLast checked
Plan a trip to Chicago
A big-museum, big-architecture city with the best restaurant value of any major US metro. Come in September. Summer and early fall are when you get the city at its best, and one September evening on a rooftop is the argument for the whole trip.
- Weekend getaways
- Food trips
- Architecture
- Families
Free to run, and you keep editing after. Add who's coming or a pace like “slow mornings” to shape the result.
Chicago at a glance
You want Chicago in 3 to 4 days, which is enough time to start with Art Institute of Chicago and let the rest fall in around it. Pick between West Loop, Wicker Park, and Lincoln Park for a base, and read the month notes before you book a flight. The three remaining stops fit in where they land. It all goes onto one map you can send to whoever is coming.
- How long
- 3–4 days
- When to go
- June to October. September is the sweet spot, with warm days and thinner crowds. January and February sit below freezing for weeks, and because the wind comes off the lake, it feels worse than the forecast reads.
- Getting around
- The L covers the city and runs from both airports. Walk the Loop and River North. Skip the car, because downtown parking is expensive and the lakefront path beats driving anyway.
What to build the plan around
- 1
Art Institute of Chicago
One of the strongest collections in the country, so give it two hours minimum, or three if you came for Impressionism.
- 2
Chicago Architecture Center river cruise
Ninety minutes that explain the skyline better than any walking tour, so book it first.
- 3
Millennium Park
Cloud Gate, the Pritzker Pavilion, and free summer concerts, which can mean fifteen minutes or a whole evening.
- 4
Wrigley Field
A day game in Lakeview turns into an afternoon in the neighborhood around it, if you let it.
Where to stay in Chicago
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- West Loop
- Restaurant Row on Randolph, and a ten-minute walk to the Loop when you want the museums. Browse stays in West Loop
- Wicker Park
- Bars, music, and vintage shops, with the Blue Line running straight to downtown, which keeps it cheap to get back. Browse stays in Wicker Park
- Lincoln Park
- Quieter and green, next to the free zoo and the lakefront path, which is the combination that makes it the easy call with kids. Browse stays in Lincoln Park
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More itineraries to copy
Each one opens as a map with every stop already placed.
Chicago planning questions
- How many days do you need in Chicago?
- 3 to 4 days is the usual answer, and the low end works only if you skip one of the four stops. Three days handles two museums, the river cruise, and two neighborhoods. Four lets you add a game or a beach afternoon, because yes, this city has beaches worth the trip.
- What is the best time to visit Chicago?
- June to October. September is the sweet spot, with warm days and thinner crowds. January and February sit below freezing for weeks, and because the wind comes off the lake, it feels worse than the forecast reads.
- Where should I stay in Chicago?
- Depends what you want to be able to reach on foot. West Loop: Restaurant Row on Randolph, and a ten-minute walk to the Loop when you want the museums. Wicker Park: Bars, music, and vintage shops, with the Blue Line running straight to downtown, which keeps it cheap to get back. Lincoln Park: Quieter and green, next to the free zoo and the lakefront path, which is the combination that makes it the easy call with kids. Nightly rate and walking distance pull against each other in all three, so you have to pick the version of that trade you mind least.
- How do you get around Chicago?
- The L covers the city and runs from both airports. Walk the Loop and River North. Skip the car, because downtown parking is expensive and the lakefront path beats driving anyway.
- What should I see first in Chicago?
- Go to Art Institute of Chicago early in the trip, before the days start filling up with things you booked later. One of the strongest collections in the country, so give it two hours minimum, or three if you came for Impressionism. The other three stops can go in whatever order the map makes easy, since none of them depends on the others.
- Is there a free Chicago itinerary I can copy?
- There is one on Arriv for Chicago, mapped stop by stop, with a suggested order for each day. Reading it costs nothing, though you will want your own copy once the dates are real. Copy it into a trip of your own to move things around, drop what you would skip, and send the result to whoever is coming.