Wheeling Holidays from £934

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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.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,506, price is now £934 per person
£934
per person
5 Sept - 10 Sept
found 19 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Friendly competent staff at checkin. The room and the view were spectacular. Wish we would have had time to use more of the amenities. I’d stay again if the opportunity arises.

Reviewed on 16 Jul 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,433, price is now £948 per person
£948
per person
5 Sept - 10 Sept
found 19 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,421, price is now £1,635 per person
£1,635
per person
9 Oct - 14 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £2,107, price is now £1,433 per person
£1,433
per person
9 Oct - 14 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Queen is very small but nice staff

Reviewed on 16 Jul 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,977, price is now £1,349 per person
£1,349
per person
5 Sept - 10 Sept
found 19 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,910 reviews)

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

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 £142 per night from 3 Aug to 4 Aug
£142
3 Aug - 4 Aug
includes taxes & fees
Hyatt Regency O'Hare Chicago
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 £220 per night from 6 Aug to 7 Aug
£220
6 Aug - 7 Aug
includes taxes & fees
8.4/10 Very good! (2,362 reviews)
"Mediocre room, less mediocre food."

Reviewed on 15 Jul 2026

Hilton Chicago O'Hare Airport
Comfort Suites Chicago O'Hare Airport

Comfort Suites Chicago O'Hare Airport

3 out of 5
4200 North River Road Schiller Park IL
Fully refundable
The price is £100 per night from 19 Jul to 20 Jul
£100
19 Jul - 20 Jul
includes taxes & fees
Comfort Suites Chicago O'Hare Airport
See all 2,627 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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Family Friendly Holidays

Stay near popular Wheeling attractions

Heritage Park

6.8/10 (35 reviews)
Heritage Park offers 104 acres of recreation with a scenic lake, sports fields, and miles of walking paths. Enjoy bird-watching from the 1.3-mile lakeside trail or reserve a picnic shelter for family gatherings.
See properties

What to do in Wheeling

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£19
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£31
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.

Explore a world of travel with Expedia

* 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.