Wheeling Holidays

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Wheeling Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
10 Sept - 15 Sept
found 1 day ago
Return flight included
San Francisco (SFO) to Chicago (ORD)
9.2/10 Wonderful! (1,773 reviews)
The staff at this property where the real stand out! They were so friendly and helpful every time we walked in. The hotel was in a nice area which allowed us to easily access the red line as well as a lot of places we wanted to go. We will definitely stay here again!

Reviewed on 19 Jun, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
10 Sept - 15 Sept
found 1 day ago
Return flight included
San Francisco (SFO) to Chicago (ORD)
9.4/10 Exceptional! (1,609 reviews)
Great hotel .. excellent staff

Reviewed on 16 Jun, 2025

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
10 Sept - 15 Sept
found 1 day ago
Return flight included
San Francisco (SFO) to Chicago (ORD)
9/10 Wonderful! (1,865 reviews)
Hotel is very clean with friendly staff. The pool was a highlight for the kids! Convenient location.

Reviewed on 19 Jun, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
10 Sept - 15 Sept
found 1 day ago
Return flight included
San Francisco (SFO) to Chicago (ORD)
9.2/10 Wonderful! (1,749 reviews)
A good location, modern, clean and friendly staff.

Reviewed on 19 Jun, 2025

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
10 Sept - 15 Sept
found 1 day ago
Return flight included
San Francisco (SFO) to Chicago (ORD)
8.8/10 Excellent! (2,217 reviews)
It was a pleasure staying at the Swissotel overlooking the river. Very convenient for a vacation stay and very quiet. Wonderful room.

Reviewed on 18 Jun, 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 S$198 per night from 4 Jul to 5 Jul
S$198
4 Jul - 5 Jul
includes taxes & fees
8.6/10 Excellent! (1,638 reviews)
"Great!"

Reviewed on 18 Jun, 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 S$270 per night from 12 Jul to 13 Jul
S$270
12 Jul - 13 Jul
includes taxes & fees
8/10 Very Good! (2,060 reviews)
"It was nice to be so close to the airport for our early morning flight."

Reviewed on 17 Jun, 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 S$164 per night from 30 Jun to 1 Jul
S$164
30 Jun - 1 Jul
includes taxes & fees
8.6/10 Excellent! (2,213 reviews)
"Very convenient location. Close tonthe fashion outlets and to the airport"

Reviewed on 18 Jun, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
See all 2,554 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.

Frequently asked questions

How much does a Wheeling holiday package cost?
Offering excellent value package deals from S$996 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.

Popular places to visit

Wrigley Field which includes a sporting event, a city and central business district

Wrigley Field

4.5/5(40 reviews)

Chicago’s world-renowned baseball ground, Wrigley Field is an iconic stadium where you can learn about the all-American sport and even catch a game.

Wrigley Field
McCormick Place

McCormick Place

4.5/5(36 reviews)

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Six Flags Great America which includes rides

Six Flags Great America

Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.

Six Flags Great America

What to do in Wheeling

River tour boat in Chicago

Architecture River Tour

S$63
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

S$58
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

S$31
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
See all activities in Wheeling

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.