Wheeling Trips (flight + hotel)

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Top hotels in Wheeling

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 P10,789 per night from Jul 26 to Jul 27
P10,789
P12,665 total
Jul 26 - Jul 27
includes taxes & fees
8/10 Very Good! (2,086 reviews)
"Convenient to airport after flight got cancelled not once but twice ."

Reviewed on Jul 2, 2025

Hilton Chicago O'Hare Airport
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 P9,310 per night from Aug 5 to Aug 6
P9,310
P10,612 total
Aug 5 - Aug 6
includes taxes & fees
8.6/10 Excellent! (1,701 reviews)
"I like it because I get to relax"

Reviewed on Jul 4, 2025

Hyatt Regency O'Hare Chicago
Chicago Getaway Hostel
Chicago Getaway Hostel
2 out of 5
616 W Arlington Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
8.8/10 Excellent! (1,081 reviews)
"Quick 15 minute walk from the Metro. At the airport, I purchased a 72 hour unlimited rides on the train/bus for 72 hours. Very safe, walkable neighborhood. My room was quiet, and reminded me of when I lived in the dorms in college, on a weekend when everyone went home. The window AC and ceiling fan ..."

Reviewed on Jul 2, 2025

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Chicago Getaway Hostel
See all 2,547 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

McCormick Place

McCormick Place

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
Millennium Park showing modern architecture, autumn leaves and street scenes

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
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

P2,740
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

P2,507
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

P2,507
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Wheeling

Frequently asked questions

How much does a Wheeling vacation package cost?
Offering excellent value package deals on Expedia, you'll be surprised at how little a vacation 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 vacation 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 vacation 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 vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to booking flights and accommodations separately. Better still, you can personalize 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 vacation 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 favorite 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 vacation 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.