Chicago
THE AMERICAS · CITY · ARCHITECTURE
Chicago invented the skyscraper, then spent a century proving it could do it better than anyone. The result is a downtown you look at the way you'd look at a gallery, with an 30km lakefront path in front of it and a lake that behaves like a sea. Add the best architecture boat tour on earth, a blues tradition, and a deep-dish argument you'll be dragged into.
The plan
Architecture river cruise
The Chicago Architecture Center boats, ninety minutes up three branches of the river. The single best thing to do in the city.
Art Institute of Chicago
Nighthawks, A Sunday on La Grande Jatte, and one of the great Impressionist rooms anywhere.
Millennium Park and the Bean
Free Pritzker Pavilion concerts all summer, and Cloud Gate reflecting the whole skyline.
A blues night
Buddy Guy's Legends in the South Loop or Kingston Mines in Lincoln Park, which runs until four.
The lakefront path by bike
30km of separated path from Hyde Park to Edgewater, with beaches all the way.
Book before you fly
Architecture river cruise
The Chicago Architecture Center's own boats are the ones to take; they sell out on summer weekends.
Art Institute
Timed entry, and free for Illinois residents on some evenings.
Skydeck & 360 Chicago
Both timed; 360's TILT is the gimmick, Skydeck's ledge is the view.
Getting there
Fly O'Hare (ORD) or Midway (MDW)
O'Hare is a United and American mega-hub with the Blue Line downtown in 45 minutes; Midway is Southwest's, closer, and on the Orange Line.
Take Amtrak
Union Station is the hub of the American rail network — the Empire Builder, Lake Shore Limited and California Zephyr all start here.
Getting around
The L runs 24 hours on the Red and Blue lines. Buy a Ventra day pass; never rent a car for a city stay.
When to go
Best time to go
May to June and September to October — warm, the lakefront is open, and the humidity hasn't arrived or has left.
Cheapest months
January to March, when it's genuinely brutal outside and hotels give rooms away.
Priciest & busiest
July and August for festivals and Lollapalooza, and the highest rates of the year.
If you've got one day
Morning
Architecture river cruise
Late morning
Art Institute of Chicago
Lunch
Portillo's
Afternoon
Millennium Park and the Bean
Evening
Dinner at Alinea, then A blues night
If you've got a week
Day 1
Arrive, settle in around The Langham Chicago, and take it slowly — Portillo's for dinner.
Day 2
Architecture river cruise.
Day 3
Art Institute of Chicago. Dinner at Alinea.
Day 4
Day trip — Milwaukee.
Day 5
Millennium Park and the Bean. Lou Malnati's at some point.
Day 6
A blues night.
Day 7
The lakefront path by bike. Finish with Girl & the Goat.
Staying longer?
Nearby & day trips
Milwaukee
Ninety minutes north by train for the Calatrava art museum and a very good beer city.
Indiana Dunes
An hour east — a national park of sand dunes on Lake Michigan with the skyline across the water.
Starved Rock
Ninety minutes southwest, canyons and waterfalls in the flattest state in America.
The full episode drops on our socials — follow along: