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.

Find the Best Holiday Packages - Chicago Holiday Package

Top Chicago Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.

Hotel Saint Clair- Magnificent Mile

Downtown Chicago

£1,107

per person

30 Sept - 5 Oct

found 1 day ago

Return flight included

Edinburgh (EDI) to Chicago (ORD)

8.4/10 Very good! (2,006 reviews)

It was convenient, very close to a lot of restaurants and shops.

Reviewed on 8 Jul 2026

Level Chicago – Old Town

Downtown Chicago

Save 100% on your flight

£1,969

per person

12 Sept - 19 Sept

found 17 hours ago

Return flight included

London (LON) to Chicago (ORD)

9/10 Wonderful! (497 reviews)

Wonderful amenities, clean and great location. The only thing I did not care for was checking myself in. Front staff welcome you but you have to complete your own check in. After a long day if travel the last thing a person wants to do is complete forms. Lowers the Luxury feel of the property when the front desk does not do what an average Holiday Inn does.

Reviewed on 6 Jul 2026

Trump International Hotel & Tower Chicago

Downtown Chicago

£1,589

per person

30 Sept - 5 Oct

found 1 day ago

Return flight included

Edinburgh (EDI) to Chicago (ORD)

9.6/10 Exceptional! (1,910 reviews)

Big five star

Reviewed on 7 Jul 2026

The Emily Hotel

Downtown Chicago

£1,242

per person

30 Sept - 5 Oct

found 24 hours ago

Return flight included

Edinburgh (EDI) to Chicago (ORD)

9.2/10 Wonderful! (1,323 reviews)

Thompson Chicago, by Hyatt

Downtown Chicago

£1,382

per person

30 Sept - 5 Oct

found 1 day ago

Return flight included

Edinburgh (EDI) to Chicago (ORD)

9.2/10 Wonderful! (1,388 reviews)

Great stay , great location

Reviewed on 6 Jul 2026

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

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	25.7°F (-3.5°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low
February	27.0°F (-2.8°C)	Light Rain	Mostly Cloudy	Slightly Low	Slightly Low
March	37.0°F (2.8°C)	Light Rain	Mostly Cloudy	Average	Average
April	46.0°F (7.8°C)	Light Rain	Mostly Sunny	Slightly Low	Average
May	57.0°F (13.9°C)	Light Rain	Mostly Sunny	Average	Average
June	67.3°F (19.6°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	73.4°F (23.0°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	73.0°F (22.8°C)	Light Rain	Mostly Sunny	Slightly High	Average
September	67.1°F (19.5°C)	Light Rain	Mostly Sunny	Average	Slightly High
October	54.9°F (12.7°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	42.3°F (5.7°C)	Light Rain	Mostly Sunny	Average	Average
December	33.1°F (0.6°C)	Light Rain	Mostly Cloudy	Average	Slightly 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.

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

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

Omni Chicago Hotel

676 N Michigan Ave Chicago IL

Fully refundableReserve now, pay when you stay

£238

26 Jul - 27 Jul

includes taxes & fees

9.2/10 Wonderful! (1,874 reviews)

"Convenient location and friendly staff."

Reviewed on 7 Jul 2026

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Fully refundableReserve now, pay when you stay

£146

27 Jul - 28 Jul

includes taxes & fees

8.2/10 Very good! (1,711 reviews)

"They had extra charges, when checking in to my room. Also, the couch had stains in my room and only one of us could take a shower. The shower was plugged and filled up with water. Would not drain."

Reviewed on 8 Jul 2026

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

£145

9 Jul - 10 Jul

includes taxes & fees

8/10 Very good! (10,200 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

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.

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."

See properties