8 Things To Do In Chicago Over Three Days
Chicago is the most underrated big city in America and it’s not close.
In this guide
- 1. The architecture boat tour, on day one
- 2. The Bean, early, and then keep moving
- 3. The Art Institute, for half a day
- 4. The lakefront, by bike
- 5. An observation deck, and pick the right one
- 6. A neighbourhood that isn’t downtown
- 7. The food argument, settled
- 8. The L, as transport and as a sight
- How to split three days
- When to go
- Where to stay
- Two things worth booking ahead
- Common questions
- The short version
It has better architecture than New York, a lakefront that behaves like a coastline, world-class museums, and food that isn’t just the deep dish everyone argues about. And it costs noticeably less than either coast.
Eight things, spread over three days, in an order that actually works geographically.
1. The architecture boat tour, on day one
Do this first. It’s the thing that makes the rest of the trip make sense.
Ninety minutes on the river with a guide explaining why the buildings look the way they do, and afterwards you’ll walk around the Loop actually seeing it rather than just looking up.
The Chicago Architecture Center runs the best one. Book ahead in summer, they sell out. And sit on the left going out, which gets you the better side for photos.
2. The Bean, early, and then keep moving
Cloud Gate in Millennium Park. Yes it’s the tourist thing. It’s also genuinely brilliant and takes fifteen minutes.
Go before 8am and you’ll get it almost to yourself, which is the difference between a nice photo and a photo of two hundred people’s phones.
While you’re there, walk through Lurie Garden and past the Pritzker Pavilion. Most people photograph the Bean and leave, and the rest of the park is the better bit.
3. The Art Institute, for half a day
One of the great museums anywhere, and it’s right there on Michigan Avenue.
American Gothic, Nighthawks, a stunning Impressionist collection, and the Thorne Miniature Rooms, which are tiny model interiors and are inexplicably the thing everyone remembers.
Half a day minimum. It’s far bigger than it looks from outside and trying to do it in ninety minutes is a waste of the ticket.
4. The lakefront, by bike
The Lakefront Trail runs 18 miles along Lake Michigan and it’s the thing locals actually use.
Hire a Divvy bike and ride from Navy Pier north toward Lincoln Park, or south past the Museum Campus for the skyline view that ends up on postcards.
On a warm day this is the best few hours you’ll have in Chicago, and it costs almost nothing.
▶ Watch This Before You Go
5. An observation deck, and pick the right one
Two options and they’re genuinely different.
Skydeck at Willis Tower is higher and has the glass ledges you step out onto. Busier, longer queues.
360 Chicago at the Hancock is lower but faces the lake and the skyline, so the view is arguably better, and there’s a bar.
IMO go to 360 Chicago at sunset with a drink. Skydeck if you’re travelling with kids who want the glass box.
6. A neighbourhood that isn’t downtown
This is the one that separates a good Chicago trip from a generic one.
Chicago is a city of neighbourhoods and the Loop is the least interesting part of it. Pick one and spend an afternoon.
- Pilsen for Mexican food and the murals.
- Logan Square for bars and the food scene.
- Andersonville for a low-key, walkable afternoon.
- Hyde Park for the university campus and the Robie House.
7. The food argument, settled
Deep dish is a tourist food. Locals eat it roughly never, and it’s essentially a casserole that takes 45 minutes to arrive.
Have it once if you want the experience. Lou Malnati’s is the one to pick.
But the actual Chicago food is tavern-style thin crust, cut into squares, which is what people here eat on a Friday. Plus Italian beef, plus a Chicago dog, and absolutely no ketchup on it unless you want a conversation.
8. The L, as transport and as a sight
The elevated train is how the city works and riding the Loop section is worth doing for its own sake.
The Brown Line around the Loop takes you between the buildings at second-floor height and it’s a better view than most paid attractions.
Get a Ventra card. The L goes to both airports, which makes it the cheapest airport transfer of any major US city by a wide margin.
How to split three days
Day one. Boat tour, Bean early, Art Institute in the afternoon, dinner in the Loop.
Day two. Lakefront by bike, Navy Pier if you fancy it, observation deck at sunset.
Day three. A neighbourhood, lunch there, and whatever you missed.
Three days is genuinely enough for the highlights. Four and you can add the Field Museum or a Cubs game.
When to go
May to October is the season, and September is the sweet spot. Warm, less humid than August, fewer crowds.
Winter is genuinely brutal. The wind off the lake is not a joke and the lakefront becomes unusable. It’s cheap for a reason.
Where to stay
Where you base yourself matters more in Chicago than in most American cities, because the good neighbourhoods are spread out.
The Loop puts you next to the museums and the boat tours and empties out in the evening. Convenient, not atmospheric.
River North is the sensible default. Walkable to everything downtown, plenty of restaurants, and it still has a pulse after six.
West Loop is where the food scene moved. Best eating in the city, ten minutes from the Loop, and increasingly the answer for a second visit.
Lincoln Park or Wicker Park if you want to live like a resident and take the L in. Cheaper, and you’ll see more of the actual city.
Two things worth booking ahead
The architecture boat tour, particularly at weekends between June and August. It sells out days in advance and the walk-up options are noticeably worse tours.
And any restaurant you actually care about. Chicago books up in a way that surprises people, and the best places in the West Loop go weeks out. A Tuesday is easier than a Saturday by a mile.
Common questions
Is three days enough for Chicago?
Yes for the main sights. Four if you want a game or a second museum.
Do I need a car?
No. The L and walking cover everything, and parking downtown is expensive.
Is deep dish worth it?
Once, as an experience. Tavern-style thin crust is what people actually eat.
Which observation deck?
360 Chicago for the view and the bar, Skydeck for the glass ledge.
Is Chicago safe for tourists?
The areas visitors go to are fine, and normal city awareness applies. The reputation is largely about neighbourhoods you have no reason to visit.
The short version
Boat tour first, Bean at dawn, Art Institute for half a day, the lakefront by bike, 360 Chicago at sunset, one neighbourhood, thin crust over deep dish, and the L everywhere.
Three days. Go in September.
