S$114 Cheap Flights to Wheeling

View S$114 flight on Sun, 1 Feb, 2026Opens in a new window

Popular airlines to Wheeling

  • notification illustration

    Be in the know

    Get alerts if flight prices drop or rise*
  • deals illustration

    Book smarter

    Save up to 40% on select hotels after you book a flight*
  • trophy illustration

    Earn twice

    Earn your airline miles on top of our rewards
    Sign in

Cheap round-trip flights to Wheeling

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wed, 4 Mar - Tue, 10 Mar
EWR
New York
MDW
Chicago
S$249 Return, found 13 hours ago
S$249
Return
found 13 hours ago
Select Delta flight, departing Wed, 4 Mar from New York to Chicago, returning Tue, 10 Mar, priced at S$249 found 13 hours ago
United
Sat, 17 Jan - Sun, 25 Jan
EWR
New York
ORD
Chicago
S$249 Return, found 1 day ago
S$249
Return
found 1 day ago
Select United flight, departing Sat, 17 Jan from New York to Chicago, returning Sun, 25 Jan, priced at S$249 found 1 day ago
American Airlines
Sat, 17 Jan - Sun, 25 Jan
EWR
New York
ORD
Chicago
S$282 Return, found 1 day ago
S$282
Return
found 1 day ago
Select American Airlines flight, departing Sat, 17 Jan from New York to Chicago, returning Sun, 25 Jan, priced at S$282 found 1 day ago
Korean Air
Mon, 2 Mar - Sun, 8 Mar
SIN
Singapore
ORD
Chicago
S$1,129 Return, found 13 hours ago
S$1,129
Return
found 13 hours ago
Select Korean Air flight, departing Mon, 2 Mar from Singapore to Chicago, returning Sun, 8 Mar, priced at S$1,129 found 13 hours ago
Air Canada
Thu, 29 Jan - Wed, 11 Feb
SIN
Singapore
ORD
Chicago
S$1,156 Return, found 9 hours ago
S$1,156
Return
found 9 hours ago
Select Air Canada flight, departing Thu, 29 Jan from Singapore to Chicago, returning Wed, 11 Feb, priced at S$1,156 found 9 hours ago

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

June is typically the cheapest month to fly

From S$100 - S$411 per traveller.

Find Your Flights to Wheeling CHI

Cheap flights to Wheeling (CHI)

Get started finding a cheap flight to Wheeling on Expedia by either choosing a deal on this page or using the search bar to enter your travel dates, origin airport and whether you want a return or one-way airfare. You can filter for flexibility, number of stops, airline and departure/arrival times to find the best flight for you.

We recommend using the ‘Flexible Dates’ calendar at the top of the page to see the price of plane tickets on the surrounding dates. This allows you to pick the cheapest days to fly if your trip allows flexibility and score cheap flight deals to Wheeling.

Return prices range from S$249 - S$1,156 and one-ways Wheeling start as low as S$114.

Be aware that choosing a non-stop flight can sometimes be more expensive while saving you time. And routes with connections may be available at a cheaper rate.

 

Airlines that fly to Wheeling (CHI)

You have several options for which airline you choose to travel with to Wheeling. There are 10 airlines flying into CHI: Delta, American Airlines, United, Korean Air, Japan Airlines, Air Canada. 

Cheap plane tickets may be available from different airlines at different times and with unique terms. It’s best to understand the details of each airline’s offer before judging its value.

For example, if you plan to check in a bag or bring hand baggage, it's worth checking whether the cheap airfare deal includes a baggage allowance. If not, verify whether the baggage fee is higher than the difference of other airline plane ticket deals offering free checked in/hand baggage in exchange for a slightly higher airfare. 

Additionally, your preferred frequent flyer membership programmes may influence your choice of cheap airline. Expedia allows you to enter your membership numbers during checkout to earn points from your airline and Expedia Rewards—all while getting a great deal and planning all your travel on one online platform.

 

Find the best deals

At Expedia, we source many flight deals from multiple providers, so you can easily find the best deals that are right for you. A great strategy for getting the best deals can be to make sure you book and travel at optimal times. Airfare to Wheeling (CHI) varies throughout the year based on seasonal demand. You’ll see the lowest rates for return trips to CHI in March and in February for one-ways.

 

Cancellation & flexibility

To change or cancel eligible flights, go to ‘My Trips’ and navigate to your itinerary. If you booked within the last 24 hours, you might be able to cancel your flight for free. Learn more about flight changes or cancellations from our customer service portal. Some plane tickets are available with no change fees, which you can filter for during your search.

Frequently asked questions

What is the name of Wheeling's airport?
The majority of travellers like to fly into O'Hare Intl. Airport (ORD) when visiting the bustling city of Wheeling.
How far is ORD from central Wheeling?
If you're staying in central Wheeling, it's a smart idea to work out how you'll get into the city before you land. The downtown area is about 18 kilometres from O'Hare Airport.
What airport is best to fly into Wheeling?
Flying to Wheeling means hitting the runway at either O'Hare Airport or Midway Intl. Airport (MDW). The first is 18 kilometres away from the downtown area. The second one is 40 kilometres away.
How many airlines fly to Wheeling?
There are 51 air carriers that jet into Wheeling from 237 airports around the world.
Which airlines fly to Wheeling?
In general, travellers opt to fly with United Airlines, American Airlines and Delta when going to Wheeling. The biggest proportion of these flights depart from New York, with United Airlines servicing this route the most.
How many nonstop flights are there to Wheeling?
Flying to a new place is much easier when there aren't any annoying stopovers to slow you down. If you're off to Wheeling, the good news is that there are approximately 7,564 direct flights operating each week.
Where are the most popular flights to Wheeling departing from?
Travellers often depart from New York, Washington and Dallas airports when going to Wheeling.
How long is the flight to Wheeling Airport?
If it's New York you're leaving behind, you'll be airborne for around 2 hours and 44 minutes before you touchdown in Wheeling. Tarmac to tarmac from Washington typically takes 2 hours and 15 minutes and from Dallas, the average flight time is 2 hours and 18 minutes.
How to book the cheapest flight to Wheeling?
If you want to save some cash on your Wheeling holiday, listen up! As any experienced jet-setter knows, don't leave booking until the last minute. Prices are usually highest just prior to the departure date. Also, shop around and compare your options. If your destination has several airports, you may be able to pick up a better deal by flying into one that's further away. Finally, another simple way to save some cash is be ready to book fast. If you stumble on a fantastic bargain, don't think twice — snap it up while you've got the chance.
Do you have any tips for my flight to Wheeling?
If you're poorly prepared, airports and flying can be daunting. But there's no need to worry. Follow these handy hints and enjoy a stress-free start to your holiday in Wheeling. What to pack in your hand luggage:

  • Air travel can be a cruisy experience if you take the right things. First things first, you'll need basic toiletries, such as lip balm and hand cream, a fresh set of clothes and something to read. Secondly, leave space in your carry-on bag for your phone, tablet and chargers, medications and perhaps a blow-up neck pillow as well. Lastly, and most importantly, remember to take your passport, travel papers and some money.

Do not pack the following items in your hand luggage:

  • Leave all your full-sized bottles of hair gel and hairspray in your checked luggage. Any liquids in your carry-on suitcase larger than 3.4 ounces (100 millilitres) will be confiscated. Pointed or sharp objects, like your treasured Swiss Army knife, and products which are explosive or flammable, such as aerosols and poisons, are also banned.

What to wear on a flight:

  • You'll want to choose comfort over style. Prepare for changes in temperature by donning layers, and opt for closed-toe, flat footwear like sneakers.
  • Caused by lengthy periods of inactivity, deep vein thrombosis (DVT) is a blood clotting condition that can affect some passengers on long-distance flights. Lower your risks by staying hydrated, keeping your lower limbs moving and wearing compression socks to help improve your circulation.

How to get through airport security fast when flying to Wheeling?
Being prepared before you arrive at the airport will help make your trip to Wheeling a piece of cake. Check out our handy tips for a swift journey through security:

  • Security personnel first need to check that you have a valid passport and matching travel documents before you can proceed any further. Have them ready for inspection.
  • After that, both you and your hand luggage must be X-rayed. To make the process quick and painless, remove anything that might trigger the alarms. Items such as your belt, coat and headphones need to go through the machine.
  • Your electronic devices like phones and laptops will also have to go on a tray to be scanned. Don't worry though, you'll be back online in no time.
  • Remove gels and liquids from your carry-on bag. They usually need to be sent through the X-ray separately. Each item should be in a container no larger than 3.4 ounces (100 millilitres) and everything must fit inside a quart-size (one litre), clear zip-close bag.
  • Choosing your footwear wisely can save you several precious minutes. Hiking boots are often required to be removed and X-rayed separately. Lightweight sneakers usually aren't.
  • Avoid taking prohibited items in your carry-on bag. If you have any sharp or pointed objects, pack them in your checked baggage. They won't be allowed on board and will be confiscated.

Flights to Wheeling information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Destination city name
Chicago
Return price
S$269

Trending flights to Wheeling

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.

Korean Air
Mon, 2 Mar - Sun, 8 Mar
SIN
Singapore
ORD
Chicago
S$1,129 Return, found 13 hours ago
S$1,129
Return
found 13 hours ago
Select Korean Air flight, departing Mon, 2 Mar from Singapore to Chicago, returning Sun, 8 Mar, priced at S$1,129 found 13 hours ago

Explore a world of travel with Expedia

*Available to Expedia members.