$29 Cheap Flights to Wheeling, IL

View $29 flight on Sat, May 2, 2026Opens in a new window

Popular airlines to Wheeling

  • Be in the know

    Get alerts if flight prices drop or rise*

  • Book smarter

    Save up to 30% on select hotels after you book a flight*

  • Earn twice

    Earn your airline miles on top of our OneKeyCash
    Learn about One Key

How much is the cheapest flight to Wheeling?

Prices were available within the past 7 days and start at $29 for one-way flights and $56 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, May 2 - Sun, May 3
EWR
New York
MDW
Chicago
$56 Roundtrip, found 1 hour ago
$56
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, May 2 from New York to Chicago, returning Sun, May 3, priced at $56 found 1 hour ago
Spirit Airlines
Wed, Apr 29 - Fri, May 1
LGA
New York
ORD
Chicago
$99 Roundtrip, found 1 hour ago
$99
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Wed, Apr 29 from New York to Chicago, returning Fri, May 1, priced at $99 found 1 hour ago
American Airlines
Tue, Jun 23 - Sat, Jun 27
EWR
New York
RFD
Rockford
$176 Roundtrip, found 1 hour ago
$176
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Jun 23 from New York to Rockford, returning Sat, Jun 27, priced at $176 found 1 hour ago
Delta
Fri, Jul 24 - Fri, Jul 31
LGA
New York
ORD
Chicago
$177 Roundtrip, just found
$177
Roundtrip
just found
Select Delta flight, departing Fri, Jul 24 from New York to Chicago, returning Fri, Jul 31, priced at $177 just found
United
Fri, Aug 28 - Sat, Aug 29
EWR
New York
ORD
Chicago
$177 Roundtrip, just found
$177
Roundtrip
just found
Select United flight, departing Fri, Aug 28 from New York to Chicago, returning Sat, Aug 29, priced at $177 just found

Alternative airports near Wheeling

Prices were available within the past 7 days. Prices and availability are subject to change.

Select flight to O'Hare Intl. ORD. Average driving time to city center is 20 minutes. Flights from $336
ORD
O'Hare Intl.
Average driving time to city center20 min
Flights from $336
Select flight to Midway Intl. MDW. Cheapest option available. Average driving time to city center is 45 minutes. Flights from $275
MDW
Midway Intl.
Cheapest
Average driving time to city center45 min
Flights from $275

Frequently asked questions

What month is the cheapest to fly to Wheeling?
May is the cheapest month to fly to Wheeling. Demand is lower then, so you're likely to snag a great deal. Booking your trip outside of public holidays and school breaks could also help you save.
Which US cities have the cheapest flights to Wheeling?
Score cheap flights to Wheeling from New York, Washington and Dallas. These cities generally offer the best fares to this unique destination. But bear in mind that holiday periods, stopovers and demand will also have an impact on rates, so stay flexible and book when prices are right.
Which US cities fly direct to Wheeling?
There are 150 US destinations where you can fly to Wheeling directly from. Compare the options by using the "Direct flights only" box on Expedia and find the best departure point for your trip. Here are some of the major cities to jet off from:

  • New York
  • Washington
  • Dallas
  • Boston
  • Phoenix

How to find a cheap flight to Wheeling?
To snag cheap flights to Wheeling, book in advance or travel during the off-season months of January and March. Want an insider tip? Jet off on a Thursday and save around 16% on average compared to traveling on a Sunday.* Set a price alert on the Expedia app and we'll notify you as soon as your fares drop.*Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
How to get a cheap last-minute flight to Wheeling?
Staying flexible about your plans might help you to find last-minute deals on cheap flights to Wheeling. To view all the available options, consider exploring different ticket types, changing your Wheeling trip dates, leaving from an alternative airport or going with another carrier.
How far in advance should I book a flight to Wheeling?
To pick up some of the biggest savings on domestic journeys, book your flight to Wheeling 28 days ahead of your travel dates. For international flights, book between two and four months in advance. This increases your chances of locking in your preferred departure dates and seats.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which day of the week is the cheapest day to buy a plane ticket to Wheeling?
Sundays are typically the best day to book a cheap flight to Wheeling, where you can save 8% on average compared to a Friday. If you decide to buy tickets on a Friday, be ready to pay a higher price as this is often the most expensive day.**Best day of the week to book, depart and ideal booking window recommendations based on average round-trip ticket prices for January through August 2023, sourced from Airline Reporting Corporation's (ARC) global airline sales database. Percentages noted are averages.
Which airlines fly to Wheeling?
There are 44 carriers that connect Wheeling with 216 airports all over the world. The chief gateway to this city is O'Hare Intl. Airport (ORD). Book a fare with any of these leading airlines to Wheeling:

  • United Airlines
  • American Airlines
  • Delta Air Lines
  • Alaska Airlines

Where do you fly into Wheeling?
When you're flying to Wheeling, the main airport to land at is O'Hare Intl. Airport (ORD). You can also jet into nearby hubs like Midway Intl. Airport (MDW), Lewis University Airport (LOT) or General Mitchell Intl. Airport (MKE). Another possibility to think about when you fly to Wheeling is Chicago Executive Airport (PWK).
How far is the airport from central Wheeling?
Landing at O'Hare Intl. Airport (ORD) puts you around 11 mi south of central Wheeling.
Can I save money by booking a Wheeling trip package?
Bundle your accommodations and flights and you could save hundreds of dollars. Better yet, you can add extras like tours and car rentals to your Wheeling flight and hotel package deal. With Expedia, it's simple to look after all your Wheeling travel arrangements in one place.
Can I change or cancel my flight to Wheeling?
If you booked your flight to Wheeling within the last 24 hours, you can often cancel or change it for free. After that, extra charges may apply depending on the airline's terms and conditions. For more information, visit our Customer Service Portal. Bear in mind that some flights are non-refundable, so you may be issued a credit toward a future flight rather than a direct refund. When searching on Expedia, use the "Changes included" or "No cancel fee" boxes to find tickets with flexible change policies.

*Flight schedules are subject to change.

*Available to One Key members.

 

Travel information

Destination airport
Midway Intl.
Destination airport IATA code
MDW
Destination city name
Chicago
Roundtrip price
$56

Trending flights to Wheeling

Prices were available within the past 7 days and start at $29 for one-way flights and $56 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Frontier Airlines
Sat, May 2 - Sun, May 3
EWR
New York
MDW
Chicago
$56 Roundtrip, found 1 hour ago
$56
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, May 2 from New York to Chicago, returning Sun, May 3, priced at $56 found 1 hour ago

Explore a world of travel with Expedia