Chicago Holidays from £842

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Top Chicago Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
per person
11 Sept - 16 Sept
found 6 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.2/10 Very Good! (2,069 reviews)
Item was left in room. I tried for days to get contact with front desk and security will little to no luck. They say nothing reported so I consider that as theft by staff. Very disappointing.

Reviewed on 2 Jul 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
4 Aug - 11 Aug
found 16 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
I had such a lovely staycation, and I recommend a stay here to everyone I know.

Reviewed on 26 Jun 2025

The Hoxton Chicago

The Hoxton Chicago

4 out of 5
Downtown Chicago
per person
4 Aug - 11 Aug
found 10 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The pool hours are a bit of a deal breaker. The pool closes at 4pm because they don’t want to offend their dining guests. So no relaxing swim after a day of site seeing in the heat unless you cut things short and rush back. This hotel needs to decide if it is a hotel or a dining and nightclub (a LOUD one..) destination. The staff was generally nice, but this will not be a repeat experience.

Reviewed on 29 Jun 2025

Hyatt Lodge Oak Brook Chicago

Hyatt Lodge Oak Brook Chicago

4 out of 5
per person
18 Sept - 23 Sept
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.8/10 Excellent! (1,008 reviews)
Parking lot under construction messing amd challenging to get to main entrance. Front desk staff pleasant and very helpful. Inner building lacked clear instruction to locate pool, sauna steam room. Rooms were excellent bed super comfy. Disappointed in breakfast i miss understood i thought set up was brunch. Overall ok nearby Oak Brook mall and fine eatry. Review other spa like lodges before locking into this location. Happy travels....

Reviewed on 3 Jul 2025

21c Museum Hotel Chicago

21c Museum Hotel Chicago

4 out of 5
Downtown Chicago
per person
11 Sept - 16 Sept
found 16 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.6/10 Excellent! (1,719 reviews)
Located near shopping and restaurants. Easy access to Red Line trains. Rooms were smaller than expected. Not as nice as other 21c hotels. Hallways were dark and beaten up. Service was friendly. Restaurant had great happy hour.

Reviewed on 2 Jul 2025

Where to stay in Chicago

Find the best Chicago areas and neighborhoods for the activities you enjoy most. 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

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
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £102 per night from 7 Jul to 8 Jul
£102
7 Jul - 8 Jul
includes taxes & fees
7.8/10 Good! (8,864 reviews)
"Decent stay for a few nights"

Reviewed on 3 Jul 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
The price is £219 per night from 6 Jul to 7 Jul
£219
6 Jul - 7 Jul
includes taxes & fees
9/10 Wonderful! (1,965 reviews)
"We enjoyed our stay at the Intercontinental! Great rooms. Clean. Great service. Will stay again."

Reviewed on 3 Jul 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £136 per night from 10 Jul to 11 Jul
£136
10 Jul - 11 Jul
includes taxes & fees
8.8/10 Excellent! (2,367 reviews)
"Staff were really nice and accommodating. I was able to check in early and check out late for free. The room was decent. Outdated but it was clean. Would book again."

Reviewed on 2 Jul 2025

Hilton Chicago/Magnificent Mile Suites
See all 5,277 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

Popular places to visit

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
Navy Pier

Navy Pier

4/5(125 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
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

What to do in Chicago

River tour boat in Chicago

Architecture River Tour

£36
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£33
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
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.

* 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.