Illinois, United States

Chicago

Plan two to three days for the Loop's architecture, museums and a couple of neighborhood food and music nights. Three nights for the market, the Mag Mile lights and the rinks. Below: 5 sights, 6 activities and 1 outdoor spot, plus how Chicago fits into a longer trip.

Plan Chicago with friends Browse 19 places

Places: 19
Curated routes: 2
Best season: Jun – Sep
Warmest month: July
Coolest month: January
Wettest month: May

Climate: NASA POWER 2001–2025 averages.

Things to do in Chicago

19 places from our curated routes, grouped by what you will do there. Each one has its own page with the address and full notes.

See

The landmarks we would not skip in Chicago across The Loop, Streeterville and Near North Side. 2 of them are free.

Photo: Ken Lund from Reno, Nevada, USA · CC BY-SA 2.0
See
Millennium Park
Cloud Gate, Crown Fountain and free summer concerts at Pritzker Pavilion.
Tip See Cloud Gate early morning before crowds.
- The Loop
- Free
- 60 min
- Early morning
Photo: User:TonyTheTiger · CC BY-SA 3.0
See
Art Institute of Chicago
Huge collection including Nighthawks, A Sunday on La Grande Jatte and the Thorne Miniature Rooms.
Tip Allow at least 3 hours; the Modern Wing links to Millennium Park.
- The Loop
- $$$
- 3 hr
- Weekday morning
Photo: Evan Huang · Google
See
Skydeck Chicago
Glass ledges 103 floors up in Willis Tower.
Tip Buy timed tickets online; clear afternoons have the longest views.
- The Loop
- $$$
- 75 min
- Sunset
Photo: Hbodine · CC BY-SA 4.0
See
Navy Pier
Lakefront pier with the Centennial Wheel, boat tours and skyline views.
- Streeterville
- $
- 1.5 hr
- Summer evening
See
Magnificent Mile
Michigan Avenue's shopping stretch north of the river, with about a million lights strung through its trees in winter.
Tip Walk north from the river to the Water Tower after dark, then warm up in one of the hotel lobbies.
- Near North Side
- Free
- 1.5 hr
- After dark

Do

Hands-on ways to spend time in Chicago across River North, The Loop and Lincoln Park.

Photo: Chicago's First Lady Cruises · Google
Do
Chicago Architecture Center River Cruise
90-minute docent-led boat tour of the skyscrapers along the Chicago River.
Tip Book ahead in summer; sit on the top deck.
- River North
- $$$
- 1.5 hr
- May–Oct
Photo: ajay_suresh · CC BY 2.0
Do
Chicago Riverwalk
1.25-mile path along the river's main branch with wine bars, kayak rentals and bridge views.
- The Loop
- Free
- 60 min
- Evening
Photo: Christine Zenino · CC BY 2.0
Do
Lincoln Park Zoo ZooLights
The city's free zoo turns into a light show with millions of bulbs from late November to early January.
Tip Book a timed ZooLights entry for weekend nights; weekdays are quieter.
- Lincoln Park
- $
- 1.5 hr
- After dark
Photo: Adam Jones · CC BY 2.0
Do
McCormick Tribune Ice Rink
Free outdoor rink in Millennium Park next to Cloud Gate, open from mid-November into March; skate rental extra.
Tip The city's Christmas tree stands in Millennium Park nearby.
- Millennium Park
- $
- 60 min
- Evening
Photo: Alanscottwalker · CC BY-SA 4.0
Do
Maggie Daley Park Skating Ribbon
A quarter-mile loop of ice winding over the hills of Maggie Daley Park, with the skyline rising behind it.
Tip Reserve a skate time online on weekends.
- Grant Park
- $
- 60 min
- Evening
Photo: ajay_suresh · CC BY 2.0
Do
Goodman Theatre
Chicago's oldest nonprofit theater, staging A Christmas Carol every holiday season since 1978.
Tip Book by early November for weekend shows.
- The Loop
- $$$
- 2.5 hr
- Evening

Outdoors

Trails, views and open space in and around Chicago.

Photo: Kenneth C. Zirkel · CC BY-SA 4.0
Outdoors
Lincoln Park Zoo
Free zoo set in a lakefront park, with conservatory and nature boardwalk nearby.
- Lincoln Park
- Free
- 2 hr
- Morning

Eat

4 places to eat across Lincoln Park, West Loop and The Loop, picked for groups who care about the food.

Photo: Pequod's Pizza · Google
Eat
Pequod's Pizza
Pan pizza with a caramelized cheese crust; a local favorite over tourist deep-dish spots.
Tip Expect waits at dinner; order ahead or come at lunch.
- Lincoln Park
- $$
- 75 min
- Lunch
Photo: Au Cheval · Google
Eat
Au Cheval
West Loop diner known for its stacked double cheeseburger.
Tip Put your name in and wait at a nearby Randolph Street bar.
- West Loop
- $$
- 75 min
- Late lunch
Photo: Ken Lund · CC BY-SA 2.0
Eat
The Walnut Room at Macy's
Marshall Field's 1907 dining room on State Street, where a Great Tree rises through the room each Christmas.
Tip Reservations go fast for December; the State Street holiday windows are on the way in.
- The Loop
- $$
- 75 min
- Lunch
Eat
The Berghoff
German restaurant on West Adams Street since 1898, with schnitzel, sauerbraten and its own root beer and lager.
Tip The bar holds Chicago's first liquor license issued after Prohibition.
- The Loop
- $$
- 75 min
- Dinner

Drink

1 bar or café in Uptown for coffee, a round or a nightcap.

Photo: Kenneth C. Zirkel · CC BY-SA 4.0
Drink
Green Mill Cocktail Lounge
Jazz club open since 1907, once a favorite of Al Capone, with live music nightly.
Tip Cash cover; Sunday night poetry slam is a tradition.
- Uptown
- $$
- 2 hr
- Late evening

Shop

1 shop in The Loop for browsing and souvenirs.

Photo: DR04 · CC BY 3.0
Shop
Christkindlmarket
German-style Christmas market in Daley Plaza since 1996, with wooden stalls, ornaments, bratwurst and Glühwein.
Tip Weekday evenings are calmer; there is a second location in Wrigleyville.
- The Loop
- $
- 1.5 hr
- After dark

Stay

Places to stay in Chicago in Streeterville.

Photo: w_lemay · CC BY-SA 2.0
Stay
The Drake
1920 lakefront hotel at the top of the Magnificent Mile, known for afternoon tea in the Palm Court.
Tip Holiday teas in the Palm Court book up weeks ahead.
- Streeterville
- $$$
- 60 min

How to fit Chicago into a trip

Chicago shows up on 2 of our curated routes, so you can work it into more than one kind of trip.

Stop 1 of 3
Chicago & Great Lakes
Skyline, architecture & lakeshore
Trip length
6 days
Best season
Jun – Sep
Pace
easy
- Next: Milwaukee
See the full itinerary
Stop 1 of 2
Chicago & Milwaukee
German markets, lit avenues and lakefront rinks
Trip length
5 days
Best season
Late Nov – Dec 24
Pace
easy
- Next: Milwaukee
See the full itinerary

Getting here and onward

Chicago to MilwaukeeMilwaukee is about 131 km / 81 mi away in a straight line

Distances are straight-line estimates between destination centers, not road distances.

Chicago month by month

Average daily highs run from 0°C / 32°F in January to 25°C / 77°F in July. May is the wettest month, with about 117 mm of rain. Outlined months fall in the best season on our routes.

Average daily highs, NASA POWER 2001–2025 averages. Chicago weather and the best time to visit →

Near Chicago

8 other destinations from our guides within about 300 km (186 mi), measured in a straight line.

Chicago questions, answered

How many days do you need in Chicago?

Our route notes suggest 2–3 days or 3 nights in Chicago. On our Chicago & Great Lakes route it is stop 1 of 3 in a 6-day trip. The listed visit times for our 19 places add up to roughly 27 hours, before travel between them, so you will need to choose.

What is Chicago best known for?

Plan two to three days for the Loop's architecture, museums and a couple of neighborhood food and music nights. Standouts on our list: Millennium Park (Cloud Gate, Crown Fountain and free summer concerts at Pritzker Pavilion); Art Institute of Chicago (Huge collection including Nighthawks, A Sunday on La Grande Jatte and the Thorne Miniature Rooms); Skydeck Chicago (Glass ledges 103 floors up in Willis Tower).

When is the best time to visit Chicago?

Our routes through Chicago are best Jun – Sep or Late Nov – Dec 24. NASA POWER 2001–2025 averages put the warmest highs in July (25°C / 77°F), the coolest in January (0°C / 32°F) and the most rain in May (about 117 mm).

What are the best things to do in Chicago?

Start with Millennium Park, Art Institute of Chicago, Chicago Architecture Center River Cruise, Chicago Riverwalk and Skydeck Chicago. Our guide lists 19 places in all, from 5 sights, 6 activities, 1 outdoor spot, 4 places to eat, 1 bar or café, 1 shop and 1 place to stay.

Where should a group eat in Chicago?

Our picks: Pequod's Pizza (Lincoln Park); Au Cheval (West Loop); The Walnut Room at Macy's (The Loop); The Berghoff (The Loop). Expect waits at dinner; order ahead or come at lunch (Pequod's Pizza).

What is near Chicago?

The closest destinations in our guides are The Loop & Chicago River (about 1 km / 1 mi), Lincoln Park (about 5 km / 3 mi) and Indiana Dunes (about 54 km / 34 mi). Distances are straight-line estimates, not road distances.

Plan Chicago with your crew

Open the Chicago & Great Lakes route in TripsCircle, invite friends with a link, settle which of these 19 places make the cut with a quick poll, then split costs and share one packing list.

Get TripsCircle

Plan around Chicago

Illinois travel hub
United States travel hub
Best Restaurants in Illinois 9 places
Top Things to Do in Illinois 17 places
Best Restaurants in United States 502 places
Best Bars & Cafés in United States 258 places
Top Things to Do in United States 919 places
Best Outdoor Spots in United States 326 places
Best Shopping in United States 71 places
Chicago weather by month