Chicago Holidays from £1,105

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Top Chicago Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£1,105
per person
8 Nov - 14 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
£1,404
per person
8 Nov - 14 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,553 reviews)
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
£1,163
per person
8 Nov - 14 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (518 reviews)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
£1,119
per person
8 Nov - 14 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (157 reviews)
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

Downtown Chicago
£1,174
per person
8 Nov - 14 Nov
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
8.8/10 Excellent! (2,293 reviews)
Clean rooms. The hotel rooms are a little dated but nothing too crazy. The happy hour in the restaurant was a hit! Great pricing and the service was top tier.

Reviewed on 24 Aug 2026

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

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

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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 wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

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Things to do in Chicago

Chicago is perfect for family, outdoor, and city-themed holidays, offering a vibrant mix of activities. Visitors can enjoy shopping areas, arena entertainment, and theatre performances. Key attractions include fascinating city tours, a Cubs game, outdoor activities, and live music events, ensuring a memorable experience in the Windy City.

Shopping

Experience shopping in Chicago at Woodfield Mall, a vibrant centre with entertainment and family-friendly options. Visit LEGOLAND® Discovery Center for unique gifts and enjoy the Arboretum of South Barrington, another lively mall offering a mix of shopping and entertainment for all ages.

Recreation

Wrigley Field offers a vibrant atmosphere for sports enthusiasts, where you can enjoy a game and soak in the lively energy. The Chicago Theatre provides a cultural experience with its stunning performances and romantic ambiance, perfect for a family night out. Cog Hill Golf & Country Club invites you to unwind amidst scenic outdoor beauty while enjoying a round of golf.

Adventure

Galloping Ghost is an exhilarating arcade adventure zone in Chicago, offering a vibrant atmosphere filled with classic games for all ages. Odyssey Fun World promises thrilling rides and arcade excitement, while The People's Choice Family Fun Center invites families to enjoy a delightful mix of games and activities.

Nightlife

Chicago's nightlife offers vibrant experiences with venues like Dave & Buster's, where you can enjoy drinks and fun entertainment vibes. For a romantic atmosphere, visit Kingston Mines or Blues on Halstead, both nightclubs that provide a lively mix of music and city allure.

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

Find the best attractions in Chicago

Chicago offers an ideal blend of family-friendly activities, outdoor adventures, and urban experiences. Visitors can explore urban parks, scenic beaches, and renowned universities, all while immersing themselves in the city's rich culture. For an unforgettable experience, be sure to spend time in downtown Chicago, where a wealth of attractions awaits, catering to diverse interests and providing lasting memories for all travellers.

  • Navy Pier: Experience the vibrant atmosphere of Navy Pier, a lively jetty that offers stunning views of Lake Michigan. Enjoy a variety of entertainment options, including rides, restaurants, and shops, making it perfect for a fun day out with friends or family.
  • Michigan Avenue: Known as the Magnificent Mile, Michigan Avenue is a bustling street lined with luxurious shops, fine dining, and iconic architecture. Stroll along this vibrant thoroughfare to soak up the city's dynamic energy and discover unique boutiques.
  • Millennium Park: A must-visit urban park, Millennium Park features beautiful green spaces, public art installations like the famous Cloud Gate sculpture, and family-friendly events. It's an ideal spot for relaxation and enjoying outdoor activities in the heart of the city.

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 SunnySlightly HighSlightly 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 SunnyAverageSlightly 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 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.

Chicago Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
2,720,500
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Chicago Riverwalk, Shedd Aquarium and Art Institute of Chicago

Top hotels in Chicago

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£89
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,309 reviews)
"Dated hotel but the location was walkable to Soldier Field which was helpful."

Reviewed on 24 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
£117
31 Aug - 1 Sept
includes taxes & fees
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
£220
18 Sept - 19 Sept
includes taxes & fees
8.4/10 Very good! (2,440 reviews)
"Terrible beds. We got a full size bed for a couple. It was quite worn down and squeeky. I’ve stayed in this hotel many times before and never had these kind of issues. Pitty experience"

Reviewed on 24 Aug 2026

Hilton Chicago O'Hare Airport
See all 5,366 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.
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Where to go when
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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 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 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 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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A large, modern building with a curved facade and multiple vertical windows.

United Center

8.8/10 (4,269 reviews)
Home to the Chicago Bulls and Blackhawks, United Centre electrifies with championship energy and passionate crowds. Arrive early to see the iconic Michael Jordan statue before experiencing Chicago's premier sports venue.
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What to do in Chicago

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

£35
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Chicago

Frequently asked questions

Why should I book my Chicago holiday with Expedia?
Expedia has your back for all aspects of your upcoming Chicago holiday. You'll always get the best deals around, but when you bundle your hotel, flights and/or hire car into a holiday package, you'll save even more. Want to really make the most of your escape? Add some exciting activities and tours to your package. We offer flexible cancellation policies on almost all bookings, so there's no need to worry if your travel plans change. Visit our Customer Service Portal link to discover more.
When is the best time of year to holiday in Chicago?
Chicago is very popular in March, May and June, so if you want to steer clear of the crowds, travel in December, January and February. To give you an idea of what type of weather you can experience, the daytime average temperature in January, the coolest month in Chicago, is -3ºC. The warmest time here is July, when temperatures average 23ºC.
What are the top hotels for my holiday in Chicago?
If you're thinking of staying in the Central Chicago neighbourhood, LondonHouse Chicago, Curio Collection by Hilton and Congress Plaza Hotel are great options. North Side is also a popular Chicago area. We recommend The Whitehall Hotel or Best Western Grant Park Hotel if you prefer this part of town.
How do I get a cheap holiday to Chicago?
Our Chicago holidays mean plenty of savings for the savvy wanderer. For the best deals, simply combine your hotel, flights and extras (including activities). But bargain prices are just the beginning of your next awesome adventure. When you book with Expedia, you'll have more than 400 airlines and 321,000 hotels throughout the world to pick from. Whatever your budget or style, there's a holiday here with your name on it. Learn more about how you can save money on your next holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Chicago holiday?
Make sure your holiday in Chicago is an unforgettable one by exploring its best attractions. McCormick Place, Wrigley Field, Millennium Park and Six Flags Great America are among the things worth seeing while you're here.
What are the best neighbourhoods to stay in when on holiday in Chicago?
If you want to find out what makes Chicago so popular, Hyde Park is an excellent place to get started. From this area, it's easy to access University of Chicago and Chicago Museum of Science and Industry. Another neighbourhood to consider is Central Chicago. Home to Millennium Park and Willis Tower, it's no wonder many travellers love coming here.
Do I need a visa for my Chicago holiday?
Official government websites will have all the information you need on visa requirements, application procedures and necessary documentation. Your nationality and the purpose of your visit, whether it be for tourism or work, will determine if you'll need a visa for Chicago. Also ensure your passport is up to date and has a minimum of six months validity remaining after the date of your return. Do all your travel planning well in advance to avoid any last-minute surprises.
What should I wear on my Chicago holiday?
Although everyone's style differs, it can help to have a few guidelines for what type of clothes to wear during your holiday in Chicago. We recommend browsing style blogs before you head off for inspiration on local dress codes or fashion trends. Daytime temperatures during January, Chicago's coolest month, average around -3ºC. July marks this city's warmest month when the average reaches 23ºC. Our top piece of advice? Take the guesswork out of what to pack and check the local weather conditions.
What does an Expedia Chicago holiday include?
Flights, car hires and hotels, or any combination of them — it's your pick! Whether you're headed to Chicago with the entire family or enjoying a solo break, there's a package to suit your budget and style. Once you've made your booking, why not add on some tours and experiences? Expedia features all sorts of properties, with the most sought after in Chicago being apartments and private holiday homes. With Expedia, you'll always have the flexibility and freedom to tailor your dream escape your way.
Does Expedia offer Book Now, Pay Later Chicago holidays?
We do. Expedia has teamed up with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply pick the payment plan best suited to your needs during checkout and take the stress out of budgeting for your next trip. Don't forget to bundle your accommodation, flights and car hire with Expedia to get the biggest bang for your travel buck. Take a look at our flexible payment options below:
  • Pay monthly holidays: Klarna offers manageable monthly payment plans that work for all budgets, so you can lock in that well-deserved holiday sooner.
  • No-deposit holidays: Pressing the "book now" button is much easier with this option. With no deposit required for your holiday, you can Book Now, Pay Later and get on your way.
Can I choose my airline with a Chicago Expedia holiday?
With a holiday package, you're in charge. Whether you'd like to fly to Chicago in coach or business class, simply pick from the available airline options. Expedia has access to more than 400 airline partners worldwide.

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. Flight-inclusive packages are ATOL protected.