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

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

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₹22,039 per night from 26 Jul to 27 Jul
₹22,039
₹29,378 total
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (1,869 reviews)
"Nice esthetically, comfortable, good food, great service, and great people."

Reviewed on 7 Jul 2026

Omni Chicago Hotel
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 ₹15,636 per night from 27 Jul to 28 Jul
₹15,636
₹18,591 total
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very good! (1,705 reviews)
"It was very nice, staff were amazing and helpful. The room was very clean and they also had easy access to parking."

Reviewed on 7 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 ₹15,534 per night from 8 Jul to 9 Jul
₹15,534
₹18,468 total
8 Jul - 9 Jul
includes taxes & fees
8/10 Very good! (10,199 reviews)
"Dated hotel but the rooms are kept clean, updated flooring and really nice bedding. Fantastic location downtown, less than a mile walking distance from Museum Campus."

Reviewed on 7 Jul 2026

Congress Plaza Hotel
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

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.