Chicago Trip

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Where to stay in Chicago

Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

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A river with yellow boats, a bridge, and tall buildings.

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

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A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

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A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

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A nighttime cityscape with fireworks over a body of water, a Ferris wheel, and illuminated buildings.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).

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Things to do in Chicago

Shopping

Woodfield Mall offers a vibrant shopping experience with a mix of business and family-friendly entertainment. For a unique visit, explore LEGOLAND® Discovery Center, perfect for kids and adults alike. Chicago Place Mall combines city vibes with shopping, making it a great spot for souvenirs and gifts.

Recreation

Experience the vibrant atmosphere at Wrigley Field, where you can enjoy a thrilling baseball game. For a cultural evening, the Rosemont Theatre offers captivating performances that celebrate family and romance. Unwind at House of Blues Chicago, where live music creates an electrifying backdrop for relaxation and entertainment.

Adventure

At Galloping Ghost, you can immerse yourself in a vast array of arcade games, perfect for family fun and adventure. Rainbow Falls Waterpark offers thrilling water slides and wave pools for an exciting day out. Pirates Cove Children's Theme Park provides a delightful experience with various attractions for young adventurers.

Nightlife

Chicago's nightlife offers vibrant experiences with venues like Blues on Halstead, where you can enjoy romantic city vibes and live music. For a fun night out, visit Dave & Buster's for drinks and entertainment. Kingston Mines promises an energetic atmosphere with fantastic blues performances and a lively crowd.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in Chicago

Chicago is ideal for family, outdoor, and city-themed holidays, offering a diverse range of attractions such as urban parks, modern universities, and event venues. Visitors can immerse themselves in the city's rich culture while exploring family-friendly experiences. Don't miss the vibrant downtown Chicago, where you can discover a variety of activities and sights to enhance your trip.

  • Michigan Avenue: Known as the Magnificent Mile, Michigan Avenue is a vibrant street lined with upscale shops, dining, and iconic architecture. Stroll along this bustling thoroughfare to experience the pulse of Chicago, with its blend of modern skyscrapers and historic landmarks, making it perfect for shopping and people-watching.
  • Navy Pier: A lively destination, Navy Pier offers stunning views of Lake Michigan and the city skyline. Enjoy a variety of attractions, including amusement rides, gardens, and dining options. The friendly atmosphere and scenic spots make it ideal for leisurely walks and family outings.
  • Millennium Park: This urban oasis features beautiful gardens, art installations, and the famous Cloud Gate sculpture. Perfect for families, Millennium Park provides a space for outdoor activities, concerts, and cultural events, all set against the backdrop of the city's stunning architecture.

Best time to go to Chicago

The best time to visit Chicago can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chicago falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chicago falls in January, visitor numbers are slightly low and weather is mostly cloudy with light rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January25.7°F (-3.5°C)Light RainMostly CloudySlightly LowSlightly Low
February27.0°F (-2.8°C)Light RainMostly CloudySlightly LowSlightly Low
March37.0°F (2.8°C)Light RainMostly CloudyAverageAverage
April46.0°F (7.8°C)Light RainMostly SunnySlightly LowAverage
May57.0°F (13.9°C)Light RainMostly SunnyAverageAverage
June67.3°F (19.6°C)Light RainMostly SunnyAverageSlightly High
July73.4°F (23.0°C)Light RainMostly SunnySlightly HighAverage
August73.0°F (22.8°C)Light RainMostly SunnySlightly HighAverage
September67.1°F (19.5°C)Light RainMostly SunnySlightly HighSlightly High
October54.9°F (12.7°C)Light RainMostly SunnyAverageSlightly High
November42.3°F (5.7°C)Light RainMostly SunnyAverageAverage
December33.1°F (0.6°C)Light RainMostly CloudyAverageSlightly Low

Tips to save on your trip to Chicago

  • Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Chicago.
  • Consider traveling during the off-peak season (typically December to February) for more affordable package holidays to Chicago.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Top hotels in Chicago

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
₹9,942
₹11,820 total
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,276 reviews)
"Valet parking was full but hotel staff was able to direct us to a safe alternative. The hotel is beautiful and the view of Buckingham Fountain was an added bonus"

Reviewed on 10 Aug 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
₹13,612
₹16,183 total
30 Aug - 31 Aug
includes taxes & fees
8/10 Very good! (1,973 reviews)
"Well I thought gettinso I got the hotel room through Expedia for $265. Thought I got a good deal. Oh no then the property decided to charge another $150 for fees. Which makes no sense to me. Was definitely not that great of a hotel. So this was a completely ridiculous hotel stay. Won't be back."

Reviewed on 10 Aug 2026

The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
₹21,487
₹25,224 total
5 Sept - 6 Sept
includes taxes & fees
Hilton Chicago O'Hare Airport
See all 5,365 properties in Chicago
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Chicago attractions

An aerial view of a baseball stadium surrounded by urban buildings.
Photo by © City of Chicago

Wrigley Field

9.0/10 (11,704 reviews)
Step into baseball's living museum where ivy-covered walls and a hand-operated scoreboard create timeless charm. Experience the electrifying atmosphere of Cubs games in this century-old "Friendly Confines."
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A Ferris wheel and a carousel at a fairground.

Navy Pier

9.0/10 (24,140 reviews)
This historic Chicago waterfront landmark offers panoramic lake views from its iconic Centennial Wheel. Enjoy seasonal fireworks or interactive exhibits at the Children's Museum while exploring Navy Pier.
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A large stadium surrounded by a cityscape with modern buildings.
Photo by © City of Chicago

Soldier Field

8.8/10 (7,063 reviews)
Soldier Field blends historic neoclassical columns with modern design as home to the Chicago Bears. Experience the electric atmosphere of an NFL game or take a guided tour exploring its century of sporting heritage.
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A river with boats, surrounded by tall buildings and a clear sky.

Chicago Riverwalk

9.6/10 (13,574 reviews)
This 1.25-mile urban promenade showcases Chicago's stunning architecture alongside the river. Stroll past public art installations, dine at waterfront cafés, or catch the evening Art on theMART digital projection show.
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A modern cityscape with tall buildings, a clear sky, and a tree-lined street.
Photo by © Cesar Russ Photography

McCormick Place

8.8/10 (9,822 reviews)
McCormick Place hosts major events like the Chicago Auto Show in its 2.6 million square feet of exhibition space. Arrive via the convenient Metra Electric Line station directly beneath the complex.
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A cityscape with modern skyscrapers and the Cloud Gate sculpture.

Millennium Park

9.4/10 (30,446 reviews)
Discover Chicago's artistic heart at Millennium Park, home to the reflective Cloud Gate and interactive Crown Fountain. Stroll through Lurie Garden or catch a free concert at the Jay Pritzker Pavilion.
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A roller coaster in motion against a clear blue sky.

Six Flags Great America

8.6/10 (992 reviews)
This Midwest thrill-seeker's paradise boasts 15 roller coasters and immersive themed areas. Arrive at opening to conquer popular rides, or consider a Flash Pass to maximise your adventure.
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Frequently asked questions

How much does a Chicago holiday package cost?
You'll find cheap prices on Expedia for your Chicago escape. However, a range of factors like the season, length of stay and your choice of hotel will determine how much your holiday to Chicago costs.
What are the cheapest months to go to Chicago?
December, January and February are the best times to look for cheap Chicago holiday packages. Opting to travel in quieter periods means you'll typically find lower prices on accommodation and flights.
How many days is enough for Chicago?
To fully enjoy a Chicago holiday, we recommend booking for 2 days. Divide your time between visiting Michigan Avenue, Chicago Riverwalk and other well-known attractions, on top of experiencing neighbourhoods like Central Chicago and Near North Side. If you've got some spare time, include a day trip or tour in your Chicago holiday itinerary.
Is it worth booking a holiday package to Chicago?
Chicago has everything you need for a fantastic trip — views, dining and culture are just the start. Whether you want to visit attractions like Navy Pier and Soldier Field, or take the road less traveled, you'll find plenty to do on your Chicago holiday.
How to find the best Chicago package deals?
Use Expedia's filters to find some great Chicago package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or browse for Chicago package deals in the low season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to lock in your holiday package well in advance.
Is it cheaper to book a Chicago holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll usually score a better deal than booking each component separately. And you'll still have the freedom to create a customised Chicago holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Chicago?
Secure incredible bargains by reserving your flights in advance with Expedia. If being spontaneous is more your thing, take advantage of our last-minute deals for an impromptu Chicago break.
How to plan a trip to Chicago?
  1. Choose when to travel: Check your diary and get your bags packed. Your preferred season and the activities available will also help you decide when to escape to Chicago.
  2. Set a budget: Factor in costs like flights, transportation and food when working out how much to put aside for your trip to Chicago. Then, choose a property that suits your budget, whether that's an affordable stay or a swankier getaway.
  3. Work out your trip length: Consider how long you'd like to spend discovering Chicago. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Chicago holiday package that brings all your bookings together.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.