Wheeling Holidays from £1,014

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Your Wheeling Holiday

When you organise a holiday package to Wheeling, you can relax and enjoy your getaway knowing your travel plans are in order. Uncover the wonders of this vibrant city while staying in a neighbourhood like Riverwoods, which is good for nature. A trip to Wheeling is a superb opportunity to sightsee. Be sure to visit big-name attractions such as Marriott Theatre, The Glen Club and Arlington International Racecourse. Stop daydreaming and start doing. Explore the wide range of options on Expedia today and put your Wheeling holiday plans into action!

Top Wheeling Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,554, price is now £1,014 per person
£1,014
per person
27 Oct - 31 Oct
found 24 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.

Reviewed on 25 Aug 2025

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 £2,303, price is now £1,465 per person
£1,465
per person
8 Oct - 15 Oct
found 6 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9.4/10 Exceptional! (2,087 reviews)
Loved the view from the room of Lake Michigan.

Reviewed on 25 Aug 2025

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,683, price is now £1,074 per person
£1,074
per person
8 Oct - 12 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,014 reviews)
We loved the experience! We shall come back again😊

Reviewed on 24 Aug 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Price was £2,172, price is now £1,399 per person
£1,399
per person
8 Oct - 15 Oct
found 6 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.

Reviewed on 25 Aug 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £2,020, price is now £1,307 per person
£1,307
per person
8 Oct - 15 Oct
found 6 hours ago
Return direct flight included
London (LGW) to Chicago (ORD)
8.2/10 Very Good! (2,061 reviews)
Amazing service and friendly staff! Great place and within walkable distances to near by shops.

Reviewed on 23 Aug 2025

Wheeling Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
38,100
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Rosemont Theatre, Parkway Bank Park Entertainment District and Marriott Theatre

Top hotels in Wheeling

Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road, Chicago, IL
The price is £132 per night from 19 Sept to 20 Sept
£132
19 Sept - 20 Sept
includes taxes & fees
8.4/10 Very Good! (1,130 reviews)
"It was very nice!!!!"

Reviewed on 25 Aug 2025

Marriott Chicago O'Hare
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £156 per night from 19 Sept to 20 Sept
£156
19 Sept - 20 Sept
includes taxes & fees
8.2/10 Very Good! (2,101 reviews)
Passing Thru
"Nice quiet and convenient hotel and room. Excellent staff."

Reviewed on 24 Aug 2025

Hilton Chicago O'Hare Airport
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave, Rosemont, IL
Fully refundableReserve now, pay when you stay
The price is £121 per night from 19 Sept to 20 Sept
£121
19 Sept - 20 Sept
includes taxes & fees
8.6/10 Excellent! (1,896 reviews)
"Nice hotel to stay."

Reviewed on 25 Aug 2025

Hyatt Regency O'Hare Chicago
See all 2,516 properties in Wheeling
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
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Popular places to visit

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

Wrigley Field

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

Wrigley Field
Magnificent Mile - River North which includes street scenes, signage and night scenes

Michigan Avenue

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
Navy Pier

Navy Pier

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

Navy Pier

What to do in Wheeling

River tour boat in Chicago

Architecture River Tour

£31
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

£30
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
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Wheeling

Frequently asked questions

Why should I book my Wheeling holiday with Expedia?
Expedia has you covered for every aspect of your upcoming Wheeling getaway. You'll always get the best deals around, but when you bundle your accommodation, flights and/or car hire into a holiday package, you'll score even bigger savings. Looking to really make the most of your stay? Add some exciting tours and activities to your package. Expedia offers flexible cancellation policies on most bookings, so you won't need to worry if you have to change your plans. Visit our Customer Service Portal link to learn more.
When is the best time of year to holiday in Wheeling?
If you want to experience the excitement of Wheeling during the high season, organise your trip for June, July and August. March, November and December are typically the quietest months of the year. To get an idea of what type of weather to expect, the average daytime temperature in January, the coolest time of year in Wheeling, is -4ºC. The warmest time here is July, when temperatures are around 23ºC.
What is the top hotel for my holiday in Wheeling?
Relax in comfort in Wheeling by choosing LondonHouse Chicago, Curio Collection by Hilton as your home-away-from-home and gateway to exploration.
How do I get a cheap holiday to Wheeling?
Creating your own Wheeling holiday with Expedia is a smart way to save. We offer more than 400 air carriers and 321,000 hotel options throughout the world. With such an extensive range to select from, you'll have no trouble creating your perfect getaway. Learn more about how you can save money on your holiday when you book a flight and hotel together with Expedia.
What should I do on my Wheeling holiday?
Make sure your next holiday in Wheeling is one to remember by exploring its most popular attractions. Chicago Botanic Garden, Lake Forest College, Northwestern Lake Forest Hospital and The Glen Club are some of the things you must see while you're in this city.
What is the best area to stay in when on holiday in Wheeling?
There's so much to do in Wheeling, so spend your nights close to its top sights and allow yourself more time sightseeing. Heritage Park is one place to put on your to-do list.
Do I need a visa for my Wheeling holiday?
Visa requirements for Wheeling vary depending on your nationality and reason for your visit. Make sure you check official government websites to determine if you need a visa for your trip. Here you'll also find the most up-to-date information, including details about application procedures and any supporting documentation that might be necessary. Enquire about your visa requirements in advance to ensure a hassle-free travel experience. Also make sure your passport is valid for a further six months from your planned date of return.
What should I wear on my Wheeling holiday?
Do a little research into the sorts of clothing people in Wheeling wear, and maybe even browse style blogs for some fashion inspiration. Aim to create a versatile travel wardrobe filled with pieces that work for your destination and show off your unique style. Pack your bags with confidence by checking the weather conditions in Wheeling. July brings the warmest temperatures, with daily averages of 23ºC, while January days average -4ºC, making it the coolest month.
What does an Expedia Wheeling holiday include?
Hotels, hire cars and flights — you'll find them all here. With Expedia, you can create your Wheeling package the way you like it. All you have to do is figure out exactly what you need. Once you've made your booking, why not add extras like tours and activities? The more you bundle, the bigger your savings! Private holiday homes and hotels are a couple of popular property types in Wheeling. No matter your holiday style or size of your group, you can rely on Expedia for the freedom to personalise your next escape.
Does Expedia offer Book Now, Pay Later Wheeling holidays?
Your bank balance shouldn't stop you from going on holiday, so Expedia has come up with a solution to help. Now that we've formed a 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 break. Check out these flexible payment options:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's manageable instalment plans. If paying across multiple transactions sounds right for you, pick this option during the checkout process.
  • No-deposit holidays: Clicking the "book now" button is easier with this option. With no deposit required for your holiday, you can Book Now, Pay Later and start packing your bags.

Can I choose my airline with a Wheeling Expedia holiday?
Expedia offers access to more than 400 partner airlines globally, so you certainly can. Simply choose the airline you want and put together your ideal Wheeling trip.

* 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.