Where to stay
Hotels in Chicago
Book direct on our own Chicago hotel pages — no booking fee and instant confirmation.
Heart of East Village 2-Bed 2-Bath Peaceful Oasis condo
869 North Marshfield Avenue 2s | Chicago, IL 60622, US
Spacious Modern Pilsen Retreat Sleeps 8 Near Downtown Chicago
1841 West 21st Street | Chicago, IL 60608, US
1 GB Wi-Fi 1 Reserved Parking Space Sleeps 4
3161 North Cambridge Avenue | Chicago, IL 60657, US
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At a glance
Climate
Continental
Languages
English and Spanish
Local currency
USD
(USD)
Local time
(GMT-5)
Ideal trip length
3–7 days
Cost level
4 of 5 · our research
Suggested area to stay
Magnificent Mile
Tap water
Generally described as safe to drink
Tipping
15-20% expected
What this place is for
History
95 · Outstanding
Culture
90 · Outstanding
Food
90 · Outstanding
Family
85 · Very good
Our own 0–100 ratings for this one destination. They describe a city; they are not a league table of cities.
Food to try
Deep-dish pizza
Chicago-style hot dog
Italian beef sandwich
Garrett Popcorn
When to visit Chicago
How good each month is here, on this destination's own scale. It compares months within this city, never one city against another.
Best months: July
Busiest: Jun-Aug
-
Jan30
Cold, snowy
-
Feb35
Very cold, snowy
-
Mar45
Chilly, thawing
-
Apr65
Mild, breezy
-
May80
Pleasant, blooming
-
Jun90
Warm, sunny
-
Jul95
Hot, humid
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Aug92
Warm, sunny
-
Sept85
Mild, crisp
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Oct70
Cool, colorful
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Nov50
Chilly, windy
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Dec40
Cold, festive
Things to do in Chicago
8 places worth your time, grouped by when they are at their best.
Showing 8 of 8 places ·
Best in the morning
3 places
Cloud Gate (The Bean)
Loop 0.5 hrs
Reflect on the city's skyline in this iconic public art sculpture.
Millennium Park
Loop 1.5 hrs
Wander through a vibrant urban park featuring art, music, and stunning landscapes.
Lincoln Park Zoo
Lincoln Park 2.5 hrs
Visit one of the nation's oldest free zoos, home to diverse wildlife.
Best in the afternoon
4 places
Art Institute of Chicago
Loop 3.5 hrs
Explore a vast collection of impressionist, post-impressionist, and American art.
Architectural Boat Tour
River North 1.5 hrs
Cruise the Chicago River to discover the city's famous architectural masterpieces.
Museum of Science and Industry
Hyde Park 4 hrs
Engage with interactive exhibits on science, technology, and engineering.
Navy Pier
Streeterville 3 hrs
Enjoy rides, dining, and entertainment along Lake Michigan's waterfront.
Any time of day
1 place
Willis Tower Skydeck
Loop 1 hr
Experience breathtaking panoramic views from the 103rd floor's glass ledge.
Chicago itineraries
Culture and history
3 Days in Chicago — Culture & History
Immerse yourself in the Windy City's rich past, iconic architecture, and vibrant cultural scene.
This 3-day itinerary is crafted for history buffs and culture enthusiasts eager to explore Chicago's world-renowned museums, architectural marvels, and significant historical landmarks. From ancient artifacts to modern art and legendary jazz, discover the stories that shaped this dynamic American metropolis.
3 Days
12 Stops
See the full plan
With the family
3 Days in Chicago — Family with Kids
Unforgettable adventures and iconic sights await your family in the Windy City.
Embark on a thrilling 3-day journey through Chicago, designed specifically for families with children. This itinerary balances iconic landmarks with interactive museums, animal encounters, and plenty of space for kids to play and explore. Discover the best of the Windy City, creating lasting memories for every member of your family.
3 Days
12 Stops
See the full plan
First-timer highlights
3 Days in Chicago — First-Timer Highlights
Discover the Windy City's iconic architecture, world-class museums, and vibrant culture.
This itinerary is designed for first-time visitors eager to experience Chicago's most famous landmarks and essential attractions. From architectural marvels to deep-dish delights, it offers a comprehensive taste of the city's unique charm and energy, perfect for those seeking a memorable urban adventure.
3 Days
15 Stops
See the full plan
For couples
2 Days in Chicago — Romance
Ignite your passion amidst Chicago's iconic skyline and charming cultural gems.
This luxurious 2-day itinerary is crafted for couples seeking an unforgettable romantic escape in the Windy City. From breathtaking skyline views and intimate dining experiences to world-class art and serene lakeside strolls, discover Chicago's most enchanting spots designed for connection and cherished memories.
2 Days
10 Stops
See the full plan
Outdoor and adventure
Route 66 Adventure
Chicago to Santa Monica
Embark on a classic American road trip along the historic Route 66. This scenic drive takes you through iconic landmarks, quirky roadside attractions, and stunning landscapes.
7 Days
9 Stops
See the full plan
Food and drink
2 Days in Chicago — Food & Wine
A gourmet journey through the Windy City's culinary landscape.
This 2-day itinerary is designed for foodies and wine enthusiasts eager to explore Chicago's vibrant gastronomic scene. From iconic deep-dish pizza to acclaimed fine dining and urban wineries, you'll savor the diverse flavors that make Chicago a world-class culinary destination. Perfect for those seeking a luxurious yet authentic taste of the city.
2 Days
10 Stops
See the full plan
Things to book
Tours and activities in Chicago
Guided tours, day trips and tickets to book alongside your stay.
Standard tour
Milwaukee,Miller Brewery Tour&Tasting 1-Day Tour from Chicago
Free cancellationFind deals
Standard tour
Oktoberfest Walking Brewery Tour in Malt Row
Free cancellationFind deals
Activity tour
Traveling Spoon Chicago-Style Deep Dish Pizza Private Online Cooking Class
Free cancellationFind deals
Standard tour
Night Time Bayou Booze Cruise
Free cancellationFind deals
Standard tour
2 Hour-Date Night & Sunset Cruise.
Free cancellationFind deals
Activity tour
New Orleans Fishing Charter (ClearVision Charters)
Free cancellationFind deals
Activity tour
New Orleans Fishing Charter
Free cancellationFind deals
Activity tour
New Orleans Private Fly Fishing (ClearVision Charters)
Free cancellationFind deals
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Things to do
Plan your Chicago trip
Practical ratings
Our own ratings and key insights for this destination.
Near Chicago
Straight-line distance from the centre of Chicago.
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Getaways from Chicago
Places people from Chicago travel to, from our own travel research.
