Chicago Holidays from £875

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The Latest Chicago Holiday Deals

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

The Emily Hotel

4 out of 5
Downtown Chicago
per person
28 May - 31 May
found 24 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (1,023 reviews)
Our overall stay was great. Didn't like they hold $150 day for incidentals and the $80 day parking charge. The hotel had no pool or room service. Everyone at the hotel was very nice.

Reviewed on 10 Mar 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
25 Apr - 1 May
found 20 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9/10 Wonderful! (475 reviews)
The property was beautiful and the stay was excellent.

Reviewed on 16 Mar 2025

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
24 Apr - 1 May
found 20 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
Overall excellent property. Carpet needs cleaning in room 1006

Reviewed on 10 Mar 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
28 May - 31 May
found 24 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (289 reviews)
Social rooms and gym modern and spacious.

Reviewed on 15 Mar 2025

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 May - 31 May
found 22 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,010 reviews)
Personal service is unparalleled. Every guest is made to feel special and I was no exception.

Reviewed on 10 Mar 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
28 May - 31 May
found 24 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,003 reviews)
The staff are very professional.

Reviewed on 15 Mar 2025

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

Our guide on where to stay in Chicago

Check out a few of the areas and neighbourhoods we love in Chicago Learn more about Chicago
Downtown Chicago featuring a city

Downtown Chicago

5 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.

Find hotels in Downtown Chicago

Our pick of the best Chicago Hotel Deals

River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free Wi-Fi, room service and a fitness centre. Our guests praise the helpful staff and the clean ...
8.6/10 Excellent! (3,879 reviews)
"Good location. Reasonable price."

Reviewed on 13 Mar 2025

River Hotel
L7 Chicago by LOTTE
L7 Chicago by LOTTE
4.5 out of 5
225 N Wabash Ave, Chicago, IL
Stay at this boutique hotel in Chicago. Enjoy free Wi-Fi, breakfast (surcharge) and a 24-hour fitness centre. Our guests praise the helpful staff and the clean ...
9.6/10 Exceptional! (1,870 reviews)
"Very nice"

Reviewed on 15 Mar 2025

L7 Chicago by LOTTE
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, 2 restaurants and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
7.8/10 Good! (8,573 reviews)
"Limited food around there"

Reviewed on 13 Mar 2025

Congress Plaza Hotel
See all 4,939 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.

All Inclusive Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

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.

Discover the most popular places to visit in Chicago

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

4.5/5(40 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Magnificent Mile - River North which includes street scenes, signage and night scenes

Michigan Avenue

4.5/5(14 reviews)

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue

Unmissable things to do in Chicago

Flyover in Chicago

Flyover in Chicago

£30
per adult
96% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

£39
per adult
94% of travellers recommend
Architecture River Tour
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

£35
per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
See all activities in Chicago

* 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.