Des Plaines Holidays from £827

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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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
per person
5 Oct - 8 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9/10 Wonderful! (1,000 reviews)
In my opinion you are paying for the convenience. The location hotel is perfect. You pretty much can walk to shopping centers and stores. The rooftop is awesome but is hard to get into because of outside reservations.

Reviewed on 16 Jul 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
5 Oct - 8 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Excellent stay - outstanding Director of Rooms and valet staff made my daughters wedding an amazing experience - just outstanding !!

Reviewed on 16 Jul 2025

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
8 Oct - 14 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (128 reviews)
Always a great place to stay!

Reviewed on 25 Jun 2025

Art Villa

Art Villa

5 out of 5
West Town
per person
5 Oct - 8 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
No reviews
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
5 Oct - 8 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Superb customer service, clean hotel!

Reviewed on 13 Jun 2025

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

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 £129 per night from 5 Aug to 6 Aug
£129
5 Aug - 6 Aug
includes taxes & fees
7.8/10 Good! (8,967 reviews)
Great Vacation!
"Loved Chicago and it was close to all the things we wanted to do. Able to walk everywhere and enjoy the water, parks, downtown area, etc."

Reviewed on 14 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
Fully refundable
The price is £217 per night from 10 Aug to 11 Aug
£217
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (2,029 reviews)
"Clean, great location ."

Reviewed on 12 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 £129 per night from 10 Aug to 11 Aug
£129
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (2,452 reviews)
"We had a great time here!"

Reviewed on 15 Jul 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,871 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

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 Des Plaines

River tour boat in Chicago

Architecture River Tour

£36
per adult
96% 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
94% of travellers recommend
Chicago By Night River & Lake Cruise
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.