Cheap Flights to Crestwood , IL from CA $152

View CA $152 flight on Sun, Sep. 28, 2025Opens in a new window

Popular airlines to Crestwood

How much is the cheapest flight to Crestwood?

Prices were available within the past 7 days and start at CA $152 for one-way flights and CA $223 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Air Canada
Fri, Oct. 24 - Sun, Oct. 26
YUL
Montreal
ORD
Chicago
CA $239 Roundtrip, found 2 hours ago
CA $239
Roundtrip
found 2 hours ago
Select Air Canada flight, departing Fri, Oct. 24 from Montreal to Chicago, returning Sun, Oct. 26, priced at CA $239 found 2 hours ago
Porter Airlines
Fri, Oct. 3 - Tue, Oct. 7
YUL
Montreal
MDW
Chicago
CA $239 Roundtrip, found 1 hour ago
CA $239
Roundtrip
found 1 hour ago
Select Porter Airlines flight, departing Fri, Oct. 3 from Montreal to Chicago, returning Tue, Oct. 7, priced at CA $239 found 1 hour ago
United
Fri, Oct. 31 - Mon, Nov. 3
YYZ
Toronto
ORD
Chicago
CA $248 Roundtrip, found 4 hours ago
CA $248
Roundtrip
found 4 hours ago
Select United flight, departing Fri, Oct. 31 from Toronto to Chicago, returning Mon, Nov. 3, priced at CA $248 found 4 hours ago
American Airlines
Wed, Sep. 10 - Sun, Sep. 14
YYZ
Toronto
ORD
Chicago
CA $261 Roundtrip, just found
CA $261
Roundtrip
just found
Select American Airlines flight, departing Wed, Sep. 10 from Toronto to Chicago, returning Sun, Sep. 14, priced at CA $261 just found
Air Transat
Sun, Sep. 28 - Tue, Sep. 30
YTZ
Toronto
MDW
Chicago
CA $285 Roundtrip, just found
CA $285
Roundtrip
just found
Select Air Transat flight, departing Sun, Sep. 28 from Toronto to Chicago, returning Tue, Sep. 30, priced at CA $285 just found

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

June is typically the cheapest month to fly

From CA $105 - CA $338 per traveller.

Graph displaying average flight prices per month

Expedia.ca gives you the best tools to secure great deals on flights to Crestwood. 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 Crestwood. Whatever your travel needs, you can always rely on Expedia.ca to help you find cheap flights to Crestwood.

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 Crestwood 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 Crestwood.

Looking to save even more? Get additional savings by bundling your Crestwood 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 Crestwood trip!

Frequently asked questions

What is the name of Crestwood's airport?
O'Hare Intl. Airport (ORD) is the main airport in Crestwood.
How far is O'Hare Airport from central Crestwood?
The trip from O'Hare Intl. Airport (ORD) to downtown Crestwood is fairly long. You'll have to travel 40 kilometres before you can drop your bags at your hotel in the city.
What airport is best to fly into Crestwood?
There are two major airports that service Crestwood. O'Hare Airport is around 40 kilometres from the central area, while Midway Intl. Airport (MDW) is around 14 kilometres away. Once you find a great price and book a place to stay, you'll have more of an idea of which one you should touchdown at.
How many airlines fly to Crestwood?
Crestwood is serviced by 51 airlines from at least 237 airports around the world.
Which airlines fly to Crestwood?
In general, travellers opt to fly with United Airlines, American Airlines and Delta when going to Crestwood. The majority of these flights depart from New York, with United Airlines operating this route the most.
How many nonstop flights are there to Crestwood?
Flying to a new place is much more fun when there aren't any lengthy stopovers. If you're jetting off to Crestwood, the fantastic news is that there are roughly 7,564 nonstop flights operating each week.
Where are the most popular flights to Crestwood departing from?
The most popular flights to Crestwood set off from New York, Washington and Dallas airports.
How long is the flight to Crestwood Airport?
If you're heading to Crestwood from New York, you're looking at a flight duration of 2 hours and 44 minutes. Those jetting off from Washington can expect to be airborne for 2 hours and 15 minutes. From Dallas it's 2 hours and 18 minutes away.
How to book the cheapest flight to Crestwood?
If you want to save some cash on your trip to Crestwood, listen up! As every seasoned jet-setter will tell you, avoid booking at the last minute. Fares are often highest just prior to the departure date. Another excellent way to get an unbeatable deal is to compare all options. If where you're headed has a few airports, don't forget to look into the cost of flying into a smaller terminal. And finally, don't forget that the early bird catches the worm. Know what a typical airfare costs and have your credit card ready to buy your ticket as soon as you spot a bargain. The best deals never last long.
Do you have any tips for my flight to Crestwood?
Depending on where you're coming from, your trip to Crestwood could be simple and straightforward or it could go on forever. Here are some tips that will help you start your next big adventure on a positive note. What to pack in your hand luggage:

  • The secret to having a worry-free travel experience is to pack ahead. Start with the essentials: passport, travel docs, cash and daily medications. Next, take on board items that'll help keep you entertained, like some electronic devices or a juicy novel. It's also a wise idea to pack your chargers, a comfy neck pillow and a pair of earphones. Finally, be sure to squeeze in toiletries like a toothbrush, deodorant and a spare set of clothes.

Do not pack the following items in your hand luggage:

  • Make sure you don't have a sharp object hiding in the bottom of your hand luggage. Other prohibited items include flammable or explosive products, such as fuel and fireworks, and gels and liquids in containers with a capacity of more than 3.4 ounces (100 millilitres).

What to wear on a flight:

  • You'll want to choose comfort over style. Prepare for temperature changes by wearing layers, and opt for slightly roomy, flat shoes like sneakers.
  • Deep vein thrombosis (DVT) can pose a risk on long-distance flights. It's the result of blood clots forming due to poor circulation, so do some gentle foot and leg exercises in your seat and consider wearing compression socks or tights.

How to get through airport security fast when flying to Crestwood?
The answer is --- be prepared. We've compiled some top tips for a stress-free trip through security. Look out Crestwood, here you come:

  • Be sure to have your ID and boarding pass at hand. They'll be the first things you'll be asked to present to security.
  • Time to strip down. Well sort of. Your coat, belt, keys and other contents of your pockets, like your earphones, will need to go on a tray through the X-ray machine. Make the whole process faster by removing them before your turn.
  • For just a few moments, you'll have to unplug from the digital world. Your laptop, phone and any other electronic gadgets will need to go through the scanner.
  • Travelling with your favourite cologne or perfume? Not a problem. As long as it's in a container no larger than 3.4 ounces (100 millilitres) and it's stored in a clear zip-close bag, it's fine to bring with you on board.
  • It's also possible you'll be asked to remove your shoes to be X-rayed, so wearing slip-on sneakers is always a clever idea.
  • 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.

Flights to Crestwood information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Destination city name
Chicago
Roundtrip price
CA $223

Trending flights to Crestwood

Prices were available within the past 7 days and start at CA $152 for one-way flights and CA $223 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

United
Sat, Nov. 1 - Sat, Nov. 1
YYZ
Toronto
ORD
Chicago
CA $223 Roundtrip, found 3 days ago
CA $223
Roundtrip
found 3 days ago
Select United flight, departing Sat, Nov. 1 from Toronto to Chicago, returning Sat, Nov. 1, priced at CA $223 found 3 days ago
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