Cheap Flights to Wheeling , IL from CA $152

View CA $152 flight on Sat, Oct. 4, 2025Opens in a new window

Popular airlines to Wheeling

  • Plan, book, fly with confidence

  • trending down icon

    Be in the know

    Get alerts if flight prices drop or rise*
  • bex rewards loyalty icon

    Book smarter

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

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

How much is the cheapest flight to Wheeling?

Prices were available within the past 7 days and start at CA $152 for one-way flights and CA $243 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Sat, Sep. 13 - Sun, Sep. 14
YTZ
Toronto
ORD
Chicago
CA $243 Roundtrip, found 4 hours ago
CA $243
Roundtrip
found 4 hours ago
Select Air Canada flight, departing Sat, Sep. 13 from Toronto to Chicago, returning Sun, Sep. 14, priced at CA $243 found 4 hours ago
Porter Airlines
Tue, Sep. 23 - Fri, Sep. 26
YTZ
Toronto
MDW
Chicago
CA $243 Roundtrip, found 4 hours ago
CA $243
Roundtrip
found 4 hours ago
Select Porter Airlines flight, departing Tue, Sep. 23 from Toronto to Chicago, returning Fri, Sep. 26, priced at CA $243 found 4 hours ago
United
Fri, Nov. 21 - Mon, Nov. 24
YYZ
Toronto
ORD
Chicago
CA $244 Roundtrip, found 1 hour ago
CA $244
Roundtrip
found 1 hour ago
Select United flight, departing Fri, Nov. 21 from Toronto to Chicago, returning Mon, Nov. 24, priced at CA $244 found 1 hour ago
American Airlines
Fri, Oct. 31 - Mon, Nov. 3
YYZ
Toronto
ORD
Chicago
CA $261 Roundtrip, just found
CA $261
Roundtrip
just found
Select American Airlines flight, departing Fri, Oct. 31 from Toronto to Chicago, returning Mon, Nov. 3, priced at CA $261 just found
Air Transat
Fri, Sep. 5 - Sat, Sep. 13
YTZ
Toronto
MDW
Chicago
CA $285 Roundtrip, found 5 days ago
CA $285
Roundtrip
found 5 days ago
Select Air Transat flight, departing Fri, Sep. 5 from Toronto to Chicago, returning Sat, Sep. 13, priced at CA $285 found 5 days ago

Find the cheapest month to fly from Columbus (CMH) to Chicago (ORD)

June is typically the cheapest month to fly

From CA $105 - CA $339 per traveller.

Graph displaying average flight prices per month

Expedia.ca gives you the best tools to secure great deals on flights to Wheeling. Use our easy and convenient booking engine to browse nonstop flights and convenient departure points every day of the year. Search airfares from the top airlines to book your perfect flight to Wheeling. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Wheeling.

Using our booking engine is simple - just type in your points of travel and preferred dates and Expedia.ca does the rest! If your travel times are flexible, you can find even better bargains by adjusting your flight dates. Browse connecting flights to increase your chances of finding even lower fares. Thanks to Expedia's Best Price Guarantee, you can book your Wheeling flights with full confidence knowing that you've found the best deal online.

Expedia.ca makes the booking process easy and stress-free by offering support along the entire way. Our friendly staff is available 24 hours a day to provide assistance and help you book your ticket. Call us toll-free at 1-888-397-3342 to answer any questions that you may have about your trip to Wheeling.

Looking to save even more? Get additional savings by bundling your Wheeling flight with a hotel and/or car rental to create a bargain travel package. Early birds can discover terrific savings by booking in advance while last minute travelers can enjoy great last minute deals. With Expedia.ca, there's no shortage of options to save even more on your Wheeling trip!

Frequently asked questions

What is the name of Wheeling's airport?
The majority of people like to fly into O'Hare Intl. Airport (ORD) when visiting the lively city of Wheeling.
How far is O'Hare Intl. Airport (ORD) from central Wheeling?
O'Hare Airport is 18 kilometres from downtown Wheeling, so you'll have a reasonable commute into the centre.
What airport is best to fly into Wheeling?
Before booking tickets to Wheeling, it's a good idea to work out which airport is the most convenient for you. ORD is 18 kilometres from downtown. If you hit the runway at Midway Airport, you'll find yourself 40 kilometres away from the city centre.
How many airlines fly to Wheeling?
There are 51 air carriers that fly into Wheeling from 237 worldwide airports.
Which airlines fly to Wheeling?
In general, travellers choose to fly with United Airlines, American Airlines and Delta when heading off to Wheeling. The majority of these flights arrive from New York, with United Airlines operating this route the most frequently.
How many nonstop flights are there to Wheeling?
Arranging an unforgettable Wheeling adventure is a piece of cake when there are 7,564 nonstop flights every week to choose from.
Where are the most popular flights to Wheeling departing from?
Flights to Wheeling departing from New York, Washington and Dallas airports are always popular.
How long is the flight to Wheeling Airport?
If you're flying to Wheeling from New York, you're looking at a flight time of 2 hours and 44 minutes. Those departing from Washington can expect to be in the air for 2 hours and 15 minutes. From Dallas it's about 2 hours and 18 minutes away.
How to book the cheapest flight to Wheeling?
If you want to have some extra spending money on your Wheeling vacation, then listen up! As every seasoned traveller will tell you, don't leave booking until the last minute. Fares are often highest close to the departure date. Don't stop there, however. Do some research and check if there are a couple of airports at your destination. Prices often differ depending on the airport you jet into. Remember to compare prices across airlines too. Last but not least, be ready to secure your seat quickly if you find an irresistible price. It might not be available for long. With a bit of know-how and some luck, the ideal fare will be yours.
Do you have any tips for my flight to Wheeling?
Depending on where you're coming from, your trip to Wheeling could be completely painless or it could drag on forever. Here are some useful hints that will help you start your next great escape on the right foot. What to pack in your hand luggage:

  • Travelling on a plane can be a cruisy experience if you take the right stuff. First things first, you'll need basic toiletries, such as a toothbrush and lip balm, a spare change of clothes and a good book. Secondly, leave space in your bag for your mobile phone, a charger, any medications and maybe a proper neck pillow too. Last, but definitely not least, don't forget to take your passport, travel docs and your credit cards.

Do not pack the following items in your hand luggage:

  • Make sure you don't have a pocket knife hiding in your carry-on luggage. Other prohibited items include explosive or flammable products, such as fuel and matches, and liquids and gels in containers with a volume of more than 3.4 ounces (100 millilitres).

What to wear on a flight:

  • Go for comfort over style. Prepare for changes in cabin temperature by layering up, and wear flat, closed-toe footwear like slip-ons.
  • Deep vein thrombosis (DVT) can pose a risk on long-distance flights. It's the result of blood clotting due to poor circulation and inactivity, so do some gentle foot and leg exercises in your seat and consider wearing compression tights or socks.

How to get through airport security fast when flying to Wheeling?
Being organized before your flight will help make your getaway to Wheeling easy and painless. Below you'll find some top tips for a speedy journey past security:

  • Your travel documents and passport will need to be inspected by airport security. Keep them handy so you don't have to dig around for them.
  • Time to strip down. Well sort of. Your jacket, belt, keys and other contents of your pockets, like your headphones, will need to go through the X-ray machine. Make your life easier by removing them as your turn draws near.
  • For just a few moments, you'll need to unplug from technology. Your laptop, phone and any other electronics also need to go through the scanner.
  • Want to bring along your favourite hand cream? No problem. As long as the volume is no larger than 3.4 ounces (100 millilitres) and it's stored in a clear zip-lock bag, you can bring it with you in your carry-on baggage.
  • Choosing your footwear wisely can save you valuable minutes. Hiking or heavy-style boots are often required to be removed and X-rayed separately. Slip-on sneakers usually aren't.
  • Airlines will not allow any sharp items or pocket knives in your carry-on baggage. If you need to bring these kinds of items, pack them in your checked baggage.

Flights to Wheeling information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Destination city name
Chicago
Roundtrip price
CA $243

Trending flights to Wheeling

Prices were available within the past 7 days and start at CA $152 for one-way flights and CA $243 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Porter Airlines
Tue, Sep. 23 - Fri, Sep. 26
YTZ
Toronto
MDW
Chicago
CA $243 Roundtrip, found 4 hours ago
CA $243
Roundtrip
found 4 hours ago
Select Porter Airlines flight, departing Tue, Sep. 23 from Toronto to Chicago, returning Fri, Sep. 26, priced at CA $243 found 4 hours ago
*Available to Expedia members.