Travel to Chicago

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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

Things to do in Chicago

Shopping

For a fantastic shopping experience in Chicago, visit Woodfield Mall, offering a vibrant mix of entertainment and family-friendly options. Don't miss the LEGOLAND® Discovery Center for unique gifts, and explore Green City Market for local produce and artisanal goods, all infused with the city's lively atmosphere.

Recreation

Experience the vibrant atmosphere at the United Center, where you can catch an exhilarating sports event. For a touch of culture and romance, enjoy a performance at the Riviera Theatre, or share laughs with family at Second City’s comedy shows, perfect for a fun-filled evening.

Adventure

Experience thrills at Rainbow Falls Waterpark, where water slides and wave pools await families and adventurers alike. At Odyssey Fun World, immerse yourself in arcade games and family fun. Launch Family Entertainment offers exciting arcade experiences, perfect for adventurous spirits seeking entertainment in Chicago.

Nightlife

In Chicago, experience vibrant nightlife at Dave & Buster's, a lively drinking pub with romantic and entertaining vibes. For a taste of the city's nightlife, visit Kingston Mines and Blues on Halstead, both energetic nightclubs offering a captivating blend of romance and city atmosphere.

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

Find the best attractions in Chicago

Chicago offers a delightful blend of family-friendly activities, outdoor adventures, and urban exploration. Visitors can enjoy a variety of attractions, including urban parks, modern universities, and event venues, all catering to those seeking cultural experiences and city life. Be sure to explore downtown Chicago for an exciting taste of the city’s vibrant atmosphere.

  • Navy Pier: Experience the vibrant atmosphere at Navy Pier, a lively jetty offering stunning waterfront views, entertainment, and dining. Stroll along the pier and soak in the urban scenery while enjoying friendly interactions with locals and other visitors.
  • Millennium Park: Discover the beauty of Millennium Park, an urban oasis perfect for families. Here, you can enjoy outdoor art installations, lush gardens, and vibrant performances, all set against the backdrop of Chicago's iconic skyline.
  • Chicago Riverwalk: Explore the picturesque Chicago Riverwalk, a scenic tourist precinct designed for leisurely strolls and family outings. Enjoy riverside dining, charming walkways, and stunning views of the city from this outdoor space.

Best time to go to Chicago

The best time to visit Chicago is dependent on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, 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

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Chicago during the low season (December to February) for more affordable options.
  • 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

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is RM545 per night from 6 Jul to 7 Jul
RM545
RM648 total
6 Jul - 7 Jul
includes taxes & fees
8.2/10 Very good! (1,689 reviews)
"We like our room, very clean and spacious"

Reviewed on 4 Jul 2026

The Chicago Hotel Collection Ambassador Gold Coast
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is RM455 per night from 8 Jul to 9 Jul
RM455
RM541 total
8 Jul - 9 Jul
includes taxes & fees
8/10 Very good! (10,156 reviews)
"Great location- good price for a holiday weekend"

Reviewed on 4 Jul 2026

Congress Plaza Hotel
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is RM1,054 per night from 6 Jul to 7 Jul
RM1,054
RM1,238 total
6 Jul - 7 Jul
includes taxes & fees
8.4/10 Very good! (2,319 reviews)
"Very convenient location for a short stay"

Reviewed on 4 Jul 2026

Hilton Chicago O'Hare Airport
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

What to do in Chicago

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.

Explore a world of travel with Expedia

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