Stories · United States
5 days in Chicago
Not a list: a thread to follow, at your own pace.
My first time in Chicago, I tried to see everything and mostly saw queues. Now I do it differently: a few places a day, the right ones, in the right order. Here is my 5-day thread.
Day 1 · The icons
To start, meet me at Wrigley Field. Take the time to walk all the way around it; the best views are rarely at the entrance. Everyone goes; everyone is right. 4.8 out of 5 across 37,021 reviews: few places are this unanimous. To get organised: here is the route by public transport; skip-the-line book your tickets, otherwise compare on Tiqets.
Late morning, I make my way to Chicago History Museum. Give it a good two hours, and leave before you are full: that is the secret to wanting to come back. Unmissable, and for good reason. Travellers give it 4.6 out of 5 (2,856 reviews) and I won’t argue with them. Practical: the public-transport route, and if you’d rather skip the queue, get your tickets in advance or go through Tiqets.
For lunch, Chicago is full of options: trust the rooms full of locals rather than the menus translated into six languages.
In the afternoon, it’s Humboldt (Alexander Von) Park. This is the breath of the trip. Even one hour changes the day. Travellers give it 4.7 out of 5 (3,932 reviews) and I won’t argue with them. Practical: how to get there, and if you’d rather skip the queue, book your visit or also check Tiqets.
In the evening, let go: a terrace, a walk, and Chicago does the rest.
Day 2 · The icons
Early in the morning, head to Chicago Riverwalk. Go late in the afternoon: the heat drops, the light softens and the photos take themselves. Everyone goes; everyone is right. Travellers give it 4.8 out of 5 (23,652 reviews) and I won’t argue with them. Practical: how to get there, and if you’d rather skip the queue, get your tickets in advance or compare on Tiqets.
Then, it’s The Wrigley Building. It’s the kind of place that makes you go quiet for a moment, even when you thought you knew it all. Travellers give it 4.7 out of 5 (4,313 reviews) and I won’t argue with them. Practical: the public-transport route, and if you’d rather skip the queue, book your visit or also check Tiqets.
At lunchtime, stay around Chicago: a noisy room, a dish of the day, and you’ve understood everything.
Later, head to Tribune Tower. You’ve seen it a hundred times in pictures; in person it is bigger, closer, more alive. 4.7 out of 5 across 1,020 reviews: few places are this unanimous. Practical: how to get there, and if you’d rather skip the queue, book your visit or go through Tiqets.
Keep the evening free. Chicago is a city that tells itself better at night.
Day 3 · Museums and culture
In the morning, it’s The Art Institute of Chicago. The audio guides are worth it; otherwise, follow a group and steal three anecdotes on the way. Unmissable, and for good reason. 4.8 out of 5 across 38,746 reviews: few places are this unanimous. Practical: how to get there, and if you’d rather skip the queue, book your tickets or also check Tiqets.
Around noon, I make my way to Crown Fountain. Take the time to walk all the way around it; the best views are rarely at the entrance. Travellers give it 4.7 out of 5 (5,635 reviews) and I won’t argue with them. Practical: here is the route by public transport, and if you’d rather skip the queue, book your visit or compare on Tiqets.
For lunch, Chicago is full of options: trust the rooms full of locals rather than the menus translated into six languages.
After lunch, it’s Millennium Park. Bring water, shoes that hold, and no watch. Everyone goes; everyone is right. Travellers give it 4.8 out of 5 (94,341 reviews) and I won’t argue with them. To get organised: how to get there; skip-the-line get your tickets in advance, otherwise also check Tiqets.
Keep the evening free. Chicago is a city that tells itself better at night.
Day 4 · The icons
To start, I make my way to Cloud Gate. Take the time to walk all the way around it; the best views are rarely at the entrance. Everyone goes; everyone is right. Travellers give it 4.7 out of 5 (42,158 reviews) and I won’t argue with them. To get organised: here is the route by public transport; skip-the-line book your visit, otherwise compare on Tiqets.
Then, I make my way to Millennium Monument. It’s the kind of place that makes you go quiet for a moment, even when you thought you knew it all. 4.7 out of 5 across 417 reviews: few places are this unanimous. Practical: here is the route by public transport, and if you’d rather skip the queue, get your tickets in advance or go through Tiqets.
For lunch, Chicago is full of options: trust the rooms full of locals rather than the menus translated into six languages.
After lunch, head to Wrigley Square. Bring water, shoes that hold, and no watch. Practical: the public-transport route, and if you’d rather skip the queue, book your tickets or compare on Tiqets.
In the evening, let go: a terrace, a walk, and Chicago does the rest.
Day 5 · Museums and culture
To start, I make my way to Griffin Museum of Science and Industry. I always pick two or three rooms rather than seeing everything. You walk out light. Everyone goes; everyone is right. 4.7 out of 5 across 36,000 reviews: few places are this unanimous. Practical: the public-transport route, and if you’d rather skip the queue, book your tickets or also check Tiqets.
Then, it’s Lincoln Park Zoo. The kids will still be talking about it weeks later. So will the adults, though they admit it less. Everyone goes; everyone is right. Travellers give it 4.6 out of 5 (40,000 reviews) and I won’t argue with them. Practical: the public-transport route · travellers’ reviews.
Lunch without a plan: the first noisy room you pass is often the right one.
After lunch, head to Willis Tower. Take the time to walk all the way around it; the best views are rarely at the entrance. Everyone goes; everyone is right. 4.5 out of 5 across 25,000 reviews: few places are this unanimous. To get organised: the public-transport route; skip-the-line get your tickets in advance, otherwise also check Tiqets.
Keep the evening free. Chicago is a city that tells itself better at night.
If you’re still hungry
I still have a few up my sleeve: Garfield Park Conservatory, Skydeck Chicago, Navy Pier, The Chicago Theatre, Chicago Cultural Center and Clarence F. Buckingham Memorial Fountain. Your call.
My advice
Walk. Then take public transport: that is where you see the city live.
Book the busiest places the day before: queues have ruined more than one morning.
Keep a little local cash: the best addresses are often the least equipped.
Safe travels. And get lost at least once; that is where Chicago begins.
A Triovol story · written by someone who would go back tomorrow
Opening hours, prices and closures change: a quick look at the venue’s website before you go avoids bad surprises.