Wheeling Holidays

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Top Flight + Hotel Deals in Wheeling

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was €1,108, price is now €813 per person
€813
per person
8 Sept - 13 Sept
found 1 day ago
Return direct flight included
Stockholm (ARN) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
Great hotel, close to a lot of tourist attractions literally walked to the bean and magnificent mile Hotel had breakfast but not that fancy but I would definitely recommend this hotel

Reviewed on 9 Jul 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was €1,465, price is now €1,069 per person
€1,069
per person
8 Sept - 13 Sept
found 1 day ago
Return direct flight included
Stockholm (ARN) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Front desk staff was super helpful and enthusiastic. Smooth check-in, and checkout.

Reviewed on 8 Jul 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was €1,289, price is now €959 per person
€959
per person
8 Sept - 13 Sept
found 1 day ago
Return direct flight included
Stockholm (ARN) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
Loved everything. One of the best hotels I have stayed in. It honestly beats some of the more expensive 5 star hotels.

Reviewed on 9 Jul 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was €2,670, price is now €2,025 per person
€2,025
per person
22 Sept - 27 Sept
found 1 day ago
Return direct flight included
Tirana (TIA) to Chicago (ORD)
9.2/10 Wonderful! (1,136 reviews)
Mediocre all around and for the price point not worth it. Great location. But nothing else compelling. Food was only ok. Service was only ok. Nothing memorable. Will seek somewhere else next time.

Reviewed on 8 Jul 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was €1,475, price is now €1,127 per person
€1,127
per person
8 Sept - 13 Sept
found 1 day ago
Return direct flight included
Stockholm (ARN) to Chicago (ORD)
9.4/10 Exceptional! (3,764 reviews)
This hotel was located perfectly to see downtown Chicago. The rooms were beautiful and the staff was wonderful. We had booked some mobility scooters to get around downtown. We had no issues getting them up to our rooms.

Reviewed on 9 Jul 2026

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 €169 per night from 3 Aug to 4 Aug
€169
3 Aug - 4 Aug
includes taxes & fees
8.8/10 Excellent! (2,809 reviews)
"Beautiful place! Loved it. Nice and clean"

Reviewed on 9 Jul 2026

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 €266 per night from 11 Jul to 12 Jul
€266
11 Jul - 12 Jul
includes taxes & fees
8.4/10 Very good! (2,334 reviews)
"Loved our stay"

Reviewed on 9 Jul 2026

Hilton Chicago O'Hare Airport
Holiday Inn Chicago North-Evanston by IHG

Holiday Inn Chicago North-Evanston by IHG

3 out of 5
1501 Sherman Ave Evanston IL
Fully refundable
The price is €126 per night from 9 Aug to 10 Aug
€126
9 Aug - 10 Aug
includes taxes & fees
8.6/10 Excellent! (2,004 reviews)
"I ALWAYS stay at this hotel when I'm in Evanston. Though I'm accustomed to the trains passing through, my partner (doesn't always travel to this hotel with me) noted that he was disturbed by the noise. I appreciate that public transit is so easily accessible. Everything is in walking distance and ..."

Reviewed on 8 Jul 2026

Holiday Inn Chicago North-Evanston by IHG
See all 2,638 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.

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

€21
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€40
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
Art Institute of Chicago

Art Institute of Chicago

€35
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Wheeling

Frequently asked questions

How much does a Wheeling holiday package cost?
Offering excellent value package deals from €813 on Expedia, you'll be surprised at how little a holiday to Wheeling costs! Our packages make travel planning easier and save you more.
What are the cheapest months to go to Wheeling?
You can usually find lower prices and greater availability in January, March and December. Explore our cheap Wheeling holiday packages and you could get some great off-season discounts.
How many days is enough for Wheeling?
With a well-planned schedule, you can easily hit the main Wheeling sights in a few days. But if you prefer to venture off the beaten track or go on day tours, consider booking your Wheeling holiday for longer.
How to find the best Wheeling package deals?
Begin your search for a Wheeling package deal by entering your preferred travel dates and destination under our "Packages" tab. Then apply some filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the ideal Wheeling package deal right away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Wheeling escape underway.
Is it cheaper to book a Wheeling holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to booking flights and accommodation separately. Better still, you can personalise your Wheeling getaway to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a holiday package to Wheeling?
If you've got your Wheeling travel dates confirmed, book as soon as you can to grab some incredible deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are great for setting off on a whim.
How to plan a trip to Wheeling?

  1. Choose your travel dates: What you'd like to do in Wheeling and your favourite season can help you decide when to go.
  2. Budget wisely: As well as the price of your hotel, you should consider other expenses. These include food, flights and transportation. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Wheeling.
  3. Decide how long to go for: Now that you're more familiar with Wheeling, you can figure out the perfect length of your break. Create a rough plan and give yourself enough time to cover everything you want to do.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to find a Wheeling holiday package that brings all your bookings together.

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.