North America

Chicago

Welcome to Chicago, where stunning architecture meets Midwestern hospitality and Lake Michigan provides a beautiful backdrop. From the iconic skyline to world-class museums, from deep-dish pizza to vibrant neighborhoods, this dynamic city offers the perfect blend of urban sophistication and friendly charm. Let our AI-powered planner help you discover the best experiences this incredible destination has to offer.

Chicago

Why Visit Chicago?

Iconic skyline and architectural masterpieces

World-class museums and cultural institutions

Famous deep-dish pizza and diverse cuisine

Beautiful Lake Michigan and waterfront

Vibrant neighborhoods and friendly culture

Perfect blend of urban sophistication and charm

Getting Around

Excellent public transportation with L trains, buses, and Metra. Walking is perfect for exploring downtown, and ride-sharing services are widely available.

Prefer renting a car? See options here.

Must-See Attractions

  • Millennium Park - Cloud Gate and outdoor art
  • Art Institute of Chicago - World-class art collection
  • Navy Pier - Lakefront entertainment
  • Magnificent Mile - Shopping and architecture
  • Wrigley Field - Historic baseball stadium
  • Chicago River - Architectural boat tours

Best Time to Visit

Weather

Chicago enjoys four distinct seasons. Summers are warm (70-85°F/21-29°C), winters are cold (20-35°F/-6-2°C), and spring/fall offer pleasant temperatures.

Best Months

May to June and September to October offer the best weather with mild temperatures, fewer crowds, and perfect conditions for sightseeing.

Peak Season

June to August brings peak tourist season with warm weather, larger crowds, and higher prices.

Off Season

November to April offers lower prices and fewer crowds, though with cold weather and occasional snow.

Popular Chicago Tours & Activities

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Top Restaurants in Chicago

Reserve a table at our hand-picked local favorites and plan dinner around your tours in Chicago.

European

AMBAR Restaurant, Chicago

Experience exceptional Balkan cuisine in Chicago with a 4.8-star rating. Discover generous portions and a welcoming atmo...

4.8$$European
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Mediterranean

Aba

Experience Aba in Chicago, a highly-rated 4.8-star Mediterranean restaurant. Discover delicious dishes and a vibrant atm...

4.8$$$Mediterranean · Fusion
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Italian

Alla Vita

Experience exceptional Italian dining in Chicago with a 4.8-star rating. Discover a warm atmosphere and memorable dishes...

4.8$$Italian
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Steakhouse & Grill

Bavette's Bar & Boeuf

Experience Chicago's premier steakhouse with a 4.7-star rating. Discover exceptional steaks, classic cocktails, and a me...

4.7$$$$Steakhouse & Grill · American
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American

Girl & The Goat

Dine at a top Chicago restaurant with a 4.7/5 rating, known for its inventive American cuisine and lively atmosphere. Pe...

4.7$$$American · Fusion
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American

The Dearborn

Experience top-tier American dining in Chicago at The Dearborn. Enjoy a 4.7-star rated meal with cocktails and live musi...

4.7$$American · Seafood
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Italian

Gibsons Italia

Experience exceptional Italian dining in Chicago with a 4.7-star rating. Revel in stunning river views and impeccable se...

4.7$$$Italian · Steakhouse & Grill
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American

STK Steakhouse

Experience Chicago's STK Steakhouse, a 4.7-star favorite for fine dining. Enjoy exceptional American cuisine, seafood, a...

4.7$$$American · Steakhouse & Grill
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American

River Roast

Dine at a top Chicago American restaurant with a 4.6 rating. Enjoy river views, great service, and delicious dishes. Res...

4.6$$American
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Mediterranean

The Purple Pig Restaurant

Dine at Chicago's acclaimed Purple Pig, a 4.6-star Mediterranean gem. Savor exceptional dishes in a vibrant atmosphere. ...

4.6$$Mediterranean · European
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American

Alinea

Experience Alinea in Chicago, a 4.6-star fine dining destination. Savor an extraordinary culinary journey with exception...

4.6$$$$American · Fusion
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American

Wildberry Pancakes & Cafe

Discover Chicago's vibrant brunch scene at Wildberry Pancakes & Cafe, boasting a 4.6-star rating. Experience delicious b...

4.6$$American
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Steakhouse & Grill

Remington's

Dine at Remington's in Chicago for acclaimed American fine dining. Enjoy a 4.6-star experience with cocktails and group-...

4.6$$Steakhouse & Grill · American
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American

Lou Mitchell's

Savor classic Chicago diner fare at Lou Mitchell's, a local favorite with a 4.6-star rating. Experience friendly service...

4.6$$American
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Asian

Time Out Market Chicago

Discover a vibrant culinary destination in Chicago's Fulton Market. Enjoy diverse food, cocktails, and rooftop views. 4....

4.5$$Asian · American
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American

Storyville Chicago

Experience 4.5-star Cajun & Creole cuisine in Chicago. Live music, cocktails, and group-friendly. Discover your new favo...

4.5$$American · Fusion
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American

Cindy's Rooftop

Dine with a 4.4-star view at this iconic Chicago rooftop. Enjoy crafted cocktails and a vibrant atmosphere. Discover why...

4.4$$$American
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Caribbean & Latin

Carnivale Chicago

Experience vibrant Chicago dining at Carnivale Chicago, rated 4.4/5. Savor creative Latin-inspired dishes in a colorful,...

4.4$$Caribbean & Latin
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European

Elephant & Castle

Experience a classic Chicago pub with a 4.3-star rating. Enjoy a warm atmosphere, outdoor seating, and cocktails. Perfec...

4.3$$European · Seafood
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Mediterranean

Beatnik On The River

Experience Mediterranean flavors by the Chicago River. This popular spot boasts a 4.1-star rating and vibrant atmosphere...

4.1$$$Mediterranean · Fusion
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Plan Your Chicago Trip

Transportation Tips

Excellent public transportation with L trains, buses, and Metra. Walking is perfect for exploring downtown, and ride-sharing services are widely available.

Car Rental Deals in Chicago

Rent a car for maximum flexibility and explore at your own pace on Expedia USA.

Where to Stay

Find the perfect accommodation for your Chicago adventure. From luxury resorts to cozy hotels, we've got you covered.

Best Hotel Deals in Chicago

Discover top-rated hotels with exclusive rates and special offers on Trivago USA.

Traveling with Kids?

Make traveling with little ones easy! Rent baby equipment in Chicago - strollers, car seats, cribs, and more delivered directly to your hotel or vacation rental. Save on baggage fees and travel light with BabyQuip.

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Frequently Asked Questions About Chicago

What is the best time to visit Chicago?

Chicago enjoys four distinct seasons. Summers are warm (70-85°F/21-29°C), winters are cold (20-35°F/-6-2°C), and spring/fall offer pleasant temperatures.

How do I get around Chicago?

Excellent public transportation with L trains, buses, and Metra. Walking is perfect for exploring downtown, and ride-sharing services are widely available.

Why should I visit Chicago?

  • Iconic skyline and architectural masterpieces
  • World-class museums and cultural institutions
  • Famous deep-dish pizza and diverse cuisine

What types of tours are available in Chicago?

Chicago offers a variety of tour experiences including:

Architecture Tours
Museum Tours
Food & Pizza Tours
Lake Michigan Tours

What are the must-see attractions in Chicago?

  • Millennium Park - Cloud Gate and outdoor art
  • Art Institute of Chicago - World-class art collection
  • Navy Pier - Lakefront entertainment
  • Magnificent Mile - Shopping and architecture
  • Wrigley Field - Historic baseball stadium
  • Chicago River - Architectural boat tours

Ready to Explore Chicago?

Discover the best tours and activities in Chicago with AI-powered recommendations tailored just for you.