Wheeling Packages (Flight + Hotel)

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Top Wheeling Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 10 hours ago
Return flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (1,115 reviews)
Spacious room with a very comfortable bed, comfortable room temperature on a hot weekend, large bathroom and spacious work station. Close to trains that transport to the loop within minutes.

Reviewed on 8 Jul 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 10 hours ago
Return flight included
Calgary (YYC) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
The servers and bartenders at the property were amazing! Gentleman who stored our luggage was polite and extremely attentive!

Reviewed on 16 Jul 2025

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 10 hours ago
Return flight included
Calgary (YYC) to Chicago (ORD)
8.6/10 Excellent! (1,795 reviews)
The TV didn't work and made a hissing sound and the tub took hours to drain after being filled. Not big deals overall, but when I mentionned it a check-out, the staff member only said sorry and did not make a note of the issues. Presumably they will get fixed when someone complains more aggressively.

Reviewed on 15 Jul 2025

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 10 hours ago
Return flight included
Calgary (YYC) to Chicago (ORD)
8.4/10 Very Good! (1,986 reviews)
For a four star hotel in chicago it is very pricy only good for location as the amenities and extras are what you gt in a 3 star hotel outside of the city. The carpet is dated and dusty, the bathroom was clean and more modern than expected, but it is not as expected.

Reviewed on 16 Jul 2025

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
per person
1 Sept - 3 Sept
found 10 hours ago
Return flight included
Calgary (YYC) to Chicago (ORD)
8.4/10 Very Good! (1,773 reviews)
Beautiful historic hotel! Loved the live music in the lobby. I was there in a traditional room sith 2 double beds, and then i upgraded to a suite. Both were nice rooms, but i LOVE a good suite! Personnel at the hotel were kind and helpful. Have a cocktail and a brownie in the lobby- you won't regret it!

Reviewed on 15 Jul 2025

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 ฿5,400 per night from 14 Aug to 15 Aug
฿5,400
฿6,155 total
14 Aug - 15 Aug
includes taxes & fees
8.6/10 Excellent! (1,738 reviews)
"Generally a very nice hotel. Escalators to lower level with not working all weekend making it difficult for people with mobility issues."

Reviewed on 15 Jul 2025

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 ฿5,820 per night from 8 Aug to 9 Aug
฿5,820
฿6,832 total
8 Aug - 9 Aug
includes taxes & fees
8/10 Very Good! (2,087 reviews)
"Very convenient. Connected on lower level with the terminal 2. Dated decor. Old bathrooms."

Reviewed on 16 Jul 2025

Hilton 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 ฿4,253 per night from 10 Aug to 11 Aug
฿4,253
฿4,848 total
10 Aug - 11 Aug
includes taxes & fees
8.6/10 Excellent! (2,291 reviews)
"My husband and I stayed in mid-June for the 1st Annual Midwest Convention (held onsite), and while the event was great, the hotel’s accessibility and amenities were seriously lacking. There was insufficient parking for wheelchair users, which created immediate challenges. My husband is in a wheelchair, ..."

Reviewed on 13 Jul 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
See all 2,562 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.

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
Millennium Park which includes autumn colours, modern architecture and street scenes

Millennium Park

4.5/5(147 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park

What to do in Wheeling

River tour boat in Chicago

Architecture River Tour

฿1,592
per adult
94% of travellers recommend
Architecture River Tour
360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

฿979
per adult
84% of travellers recommend
360 CHICAGO Observation Deck
Chicago CityPASS: Admission to Top 5 Chicago Attractions

Chicago CityPASS®: Experience 5 must-see attractions

฿4,634
per adult
92% of travellers recommend
Chicago CityPASS®: Experience 5 must-see attractions
See all activities in Wheeling

Frequently asked questions

How much does a Wheeling holiday package cost?
Offering excellent value package deals from ฿13,514 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.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.