Des Plaines Holidays from £797

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Your Des Plaines Holiday

Reserve a Des Plaines holiday package that includes everything you need and nothing you don't. Good for cafes, nature and bars and pubs, think about basing yourself in the neighbourhood of Rogers Park. If your trip to Des Plaines includes a little sightseeing, don't miss major attractions such as Allstate Arena, Rosemont Theatre and Fashion Outlets of Chicago. Stop dreaming and start adventuring. Explore the many options on Expedia today and finally put your Des Plaines holiday plans into motion!

Top Des Plaines Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was £1,019, price is now £797 per person
£797
per person
20 Jan - 24 Jan
found 21 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)
Amazing view, but basic room

Reviewed on 7 Nov 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £1,082, price is now £813 per person
£813
per person
20 Jan - 24 Jan
found 21 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
Beautiful rooms and service.

Reviewed on 5 Nov 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £2,018, price is now £1,528 per person
£1,528
per person
25 Dec - 30 Dec
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)
Beautiful hotel situated perfectly for most downtown Chicago activities. Attentive staff and amazing views from our 14th floor lake view room. This stay has been on my bucket list for awhile. This hotel experience did not disappoint

Reviewed on 6 Nov 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was £2,673, price is now £2,122 per person
£2,122
per person
25 Dec - 30 Dec
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was £1,347, price is now £1,074 per person
£1,074
per person
25 Dec - 30 Dec
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)

Des Plaines Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
58,700
Max Temp Winter
-1.11ºC
Max Temp Summer
24ºC
Top Sights
Rosemont Theatre, Parkway Bank Park Entertainment District and Riviera Theatre

Top hotels in Des Plaines

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

3 out of 5
3001 South Mannheim Road Des Plaines IL
Fully refundable
The price is £111 per night from 27 Nov to 28 Nov
£111
27 Nov - 28 Nov
includes taxes & fees
8.8/10 Excellent! (2,084 reviews)
"Long walk if you planning on attending any concert at the allstate Arena"

Reviewed on 7 Nov 2026

Holiday Inn Express & Suites Chicago O'Hare Airport by IHG
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 £103 per night from 24 Nov to 25 Nov
£103
24 Nov - 25 Nov
includes taxes & fees
Congress Plaza 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 £103 per night from 11 Nov to 12 Nov
£103
11 Nov - 12 Nov
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
See all 4,984 properties in Des Plaines
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
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Family Friendly Holidays

Stay near popular Des Plaines attractions

Rivers Casino

8.0/10 (559 reviews)
Chicagoland's premier casino offers over 1,000 slots and nearly 50 table games in a vibrant setting. Enjoy upscale dining at Hugo's Frog Bar & Chop House while taking advantage of the free on-site parking.
See properties

What to do in Des Plaines

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

£32
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Architecture River Tour from Michigan Avenue

Architecture River Tour from Michigan Avenue

£31
per adult
Architecture River Tour from Michigan Avenue
See all activities in Des Plaines

Frequently asked questions

Why should I book my Des Plaines holiday with Expedia?
Choose Expedia to organise your next escape easily and all in one place. Our insider tip for bagging an unbeatable deal on a Des Plaines retreat? Bundle your hotel, flights and/or hire car into a package holiday. Then throw in some awesome tours and activities. Most bookings also have flexible cancellation policies, so there's no need to panic if you have to change your travel plans. Round-the-clock help with amending and cancelling your trip is on-hand via our Customer Service Portal link.
When is the best time of year to holiday in Des Plaines?
Peak season falls in May, July and August and is a thrilling time to visit — but be prepared for bigger crowds and longer queues. November, December and January are usually quieter times of the year. To give you an idea of what type of weather to expect, the average temperature during the day in January, the coolest month in Des Plaines, is -4ºC. The warmest time here is July, when temperatures hit an average of 23ºC.
What is the top hotel for my holiday in Des Plaines?
LondonHouse Chicago, Curio Collection by Hilton sets the stage for an exciting escape in Des Plaines, offering all the conveniences you need and more.
How do I get a cheap holiday to Des Plaines?
If you love getting an amazing deal, combine your bookings into a Des Plaines holiday. Whether you're looking for flights, hotels, tours or hire cars, you can book everything in one place. You'll have plenty of choice at your fingertips as well. Expedia has over 400 air carriers and 321,000 hotel options around the globe to select from. Fly with who you prefer, find a room where you like and save precious pounds — now that's the ideal escape! Learn more about how you can save money on your holiday when you combine your hotel and flight bookings with Expedia.
What should I do on my Des Plaines holiday?
Offering popular attractions like Donald E. Stephens Convention Centre and Woodfield Mall, a holiday in Des Plaines is full of fun things to do and see. Allstate Arena and Schaumburg Convention Centre are two other sights worth checking out.
What is the best area to stay in when on holiday in Des Plaines?
Des Plaines has lots of wonderful places to explore, such as Rivers Casino. Book accommodation close by and make sightseeing a breeze.
Do I need a visa for my Des Plaines holiday?
Check the latest information on official government websites. Your nationality and whether you're travelling for work or pleasure will determine if you'll require a visa for Des Plaines. Get familiar with the application process, including any required documentation, turnaround times and fees. Start your application well in advance to allow sufficient time for processing. Some visas may take many weeks or even months to obtain, depending on the country and time of year.
What should I wear on my Des Plaines holiday?
Think about the types of activities you'll be doing during your holiday in Des Plaines and travel with pieces that can be mixed and matched. For fashion inspiration or even information on dress codes, browse a few style blogs or social media accounts. Daytime temperatures in January, Des Plaines's coolest month, average -4ºC. July marks this city's warmest month when the average temperature reaches 23ºC. Our top tip? Take the guesswork out of what to pack and check the weather forecast.
What does an Expedia Des Plaines holiday include?
Choose from any combination of flights, hire cars and hotels. Once you've made your booking, add some tours and activities. Want to pick your fare class? That's also possible. The choice is all yours when it comes to planning your perfect Des Plaines getaway. Private holiday homes and apartments are two of the most popular property types in Des Plaines. Whatever your holiday style or size of your group, you can count on Expedia for the flexibility to personalise your next escape.
Does Expedia offer Book Now, Pay Later Des Plaines holidays?
Your bank balance shouldn't prevent you from taking a holiday, so Expedia has come up with a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book a fantastic getaway without draining your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your trip. Check out these flexible payment options:

  • Pay monthly holidays: Escape on that dream holiday sooner with Klarna's easy instalment plans. If paying just a small amount each month works for you, choose this option during the checkout process.
  • No-deposit holidays: When you stumble on an awesome deal but your budget doesn't quite go that far, Klarna's no-deposit holiday plan will allow you to Book Now, Pay Later to lock it in.

Can I choose my airline with a Des Plaines Expedia holiday?
You can, and with more than 400 airlines to choose from all over the world, you have loads of choice. Take a look at the available options and find out which airline best fits your needs and budget.

* 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.