Wheeling Holidays from £842

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to £335 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Packages with flights are ATOL protected

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.
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 15 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

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 £141 per night from 4 Aug to 5 Aug
£141
4 Aug - 5 Aug
includes taxes & fees
8.6/10 Excellent! (1,702 reviews)
"Very nice property, note that parking is an additional charge"

Reviewed on 1 Jul 2025

Hyatt Regency O'Hare Chicago
Super 8 by Wyndham Chicago O'Hare Airport
Super 8 by Wyndham Chicago O'Hare Airport
3.5 out of 5
2951 Touhy Ave, Elk Grove Village, IL
Fully refundableReserve now, pay when you stay
The price is £69 per night from 6 Jul to 7 Jul
£69
6 Jul - 7 Jul
includes taxes & fees
7.8/10 Good! (1,285 reviews)
"Quite"

Reviewed on 30 Jun 2025

Super 8 by Wyndham Chicago O'Hare Airport
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
3.5 out of 5
5440 N River Rd, Rosemont, IL
Fully refundable
The price is £99 per night from 6 Jul to 7 Jul
£99
6 Jul - 7 Jul
includes taxes & fees
8.6/10 Excellent! (2,266 reviews)
"The staff at as very nice and helpful. The ice machine next door was flooding and had a pile of towels laying there. The carpet in the bedroom was very wet near the window."

Reviewed on 30 Jun 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
See all 2,543 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

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

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

Wrigley Field
Navy Pier

Navy Pier

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

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 Wheeling

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 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.