S$153 Cheap Flights to Oak Lawn

View S$153 flight on Fri, 27 Mar, 2026Opens in a new window

Popular airlines to Oak Lawn

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Cheap round-trip flights to Oak Lawn

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.

Air Canada
Fri, 27 Mar - Mon, 30 Mar
YYZ
Toronto
ORD
Chicago
S$240 Return, found 3 days ago
S$240
Return
found 3 days ago
Select Air Canada flight, departing Fri, 27 Mar from Toronto to Chicago, returning Mon, 30 Mar, priced at S$240 found 3 days ago
Delta
Wed, 3 Dec - Fri, 12 Dec
YYZ
Toronto
ORD
Chicago
S$275 Return, found 4 days ago
S$275
Return
found 4 days ago
Select Delta flight, departing Wed, 3 Dec from Toronto to Chicago, returning Fri, 12 Dec, priced at S$275 found 4 days ago
United
Sun, 14 Dec - Wed, 17 Dec
YYZ
Toronto
ORD
Chicago
S$298 Return, found 1 day ago
S$298
Return
found 1 day ago
Select United flight, departing Sun, 14 Dec from Toronto to Chicago, returning Wed, 17 Dec, priced at S$298 found 1 day ago
American Airlines
Sun, 14 Dec - Tue, 16 Dec
YYZ
Toronto
ORD
Chicago
S$314 Return, found 1 day ago
S$314
Return
found 1 day ago
Select American Airlines flight, departing Sun, 14 Dec from Toronto to Chicago, returning Tue, 16 Dec, priced at S$314 found 1 day ago
Icelandair
Fri, 6 Feb - Sat, 21 Feb
IST
Istanbul
ORD
Chicago
S$690 Return, found 1 day ago
S$690
Return
found 1 day ago
Select Icelandair flight, departing Fri, 6 Feb from Istanbul to Chicago, returning Sat, 21 Feb, priced at S$690 found 1 day ago

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

July is typically the cheapest month to fly

From S$101 - S$379 per traveller.

Find Your Flights to Oak Lawn CHI

Cheap flights to Oak Lawn (CHI)

Get started finding a cheap flight to Oak Lawn 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 Oak Lawn.

Return prices range from S$240 - S$1,158 and one-ways Oak Lawn start as low as S$153.

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 Oak Lawn (CHI)

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

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 Oak Lawn (CHI) varies throughout the year based on seasonal demand. You’ll see the lowest rates for return trips to CHI in March and in March 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 Oak Lawn's airport?
O'Hare Intl. Airport (ORD) is the most popular airport in Oak Lawn.
How far is ORD from central Oak Lawn?
The journey between O'Hare Airport and downtown Oak Lawn is fairly long. You'll need to travel 32 kilometres before you can check in to your city hotel.
What airport is best to fly into Oak Lawn?
Hop off the plane at O'Hare Airport and you'll find yourself 32 kilometres from the centre of town. MDW also welcomes many people to Oak Lawn. It's 8 kilometres from the city centre.
How many airlines fly to Oak Lawn?
There are 51 airlines that fly into Oak Lawn from 237 worldwide airports.
Which airlines fly to Oak Lawn?
Typically, travellers choose to fly with United Airlines, American Airlines and Delta when going to Oak Lawn. The majority of these flights depart from New York, with United Airlines flying this route the most.
How many nonstop flights are there to Oak Lawn?
Flying to a new place is much easier when there aren't any stopovers to worry about. If you're off to Oak Lawn, the fantastic news is that there are around 7,564 direct flights operating every week.
Where are the most popular flights to Oak Lawn departing from?
Travellers frequently jet off from New York, Washington and Dallas airports when flying to Oak Lawn.
How long is the flight to Oak Lawn Airport?
Which airport you depart from determines how much of the in-flight entertainment you'll get to see. From New York to Oak Lawn, the average flight time is 2 hours and 44 minutes. From Washington it usually takes 2 hours and 15 minutes, and from Dallas it's 2 hours and 18 minutes.
How to book the cheapest flight to Oak Lawn?
Don't leave locking in your flight to Oak Lawn until the last possible moment. That's one move frequent travellers use to get the best prices. Booking ahead means more choices and less expensive flights. Don't stop there, however. Do some research and check if there is more than one airport at your destination. Prices often differ depending on the airport you use. Be sure to compare prices across air carriers too. Lastly, another easy way to save a few dollars is be ready to book fast. If you see a terrific deal, don't hold off — grab it while you've got the chance.
Do you have any tips for my flight to Oak Lawn?
If you're poorly prepared, airports and flying can be challenging. But don't hit the panic button just yet. Follow these handy tips and enjoy a comfortable start to your holiday in Oak Lawn. What to pack in your hand luggage:

  • First things first, pack in your passport, travel documents, credit cards and medications. Next, you'll want some extra in-flight entertainment to help pass the time. A juicy book and a tablet crammed with your favourite movies are always good options. If you hope to take a short nap, a comfy neck pillow and some earplugs will also come in handy. Finally, squeeze in a toothbrush and some cleansing wipes to ensure you arrive looking fresh and raring to go.

Do not pack the following items in your hand luggage:

  • Check carefully that you don't have sharp or pointed objects hiding in one of the zippers of your hand luggage. Other restricted items include flammable or explosive goods, such as fuel and matches, and liquids and gels in containers larger than 3.4 ounces (100 millilitres).

What to wear on a flight:

  • Your aim is to feel as comfortable as possible. Choose shoes that are easy to slip on and off, dress in loose, breathable clothing and remember to take a pullover in case you get cold in the cabin.
  • Caused by lengthy periods of inactivity, deep vein thrombosis (DVT) is a blood clot condition that can affect passengers during long flights. Lower your risks by staying hydrated, keeping your legs and ankles moving and wearing compression socks or tights.

How to get through airport security fast when flying to Oak Lawn?
Being prepared before you arrive at the airport will make your trip to Oak Lawn a breeze. Here are some handy hints for a speedy journey past security:

  • Airport security personnel first need to make sure that you have a valid ID and travel documents before you're allowed to proceed any further. Keep them close by.
  • After that, both you and your carry-on luggage will be X-rayed. To make the process quick and painless, remove anything that might trigger the alarms. Personal belongings such as your coat, belt and headphones will be required to go through the machine.
  • For just a few moments, you'll have to unplug from technology. Your tablet, phone and any other electronic devices will need to be sent through the scanner.
  • Remove all gels and liquids from your hand luggage. They usually need to be sent through the X-ray scanner separately. Each item should be in a container no larger than 3.4 ounces (100 millilitres) and everything must fit inside a single quart-size (one litre), clear zip-close bag.
  • There's a possibility that you'll be asked to take your shoes off for scanning, so wearing slip-on shoes is always a clever idea.
  • Avoid taking prohibited items in your carry-on bag. If you have any sharp objects like a pocket knife or tools, pack them in your checked luggage. They won't be allowed in the cabin.

Flights to Oak Lawn information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Destination city name
Chicago
Return price
S$179

Trending flights to Oak Lawn

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.

Air Canada
Thu, 5 Mar - Tue, 10 Mar
SIN
Singapore
ORD
Chicago
S$1,158 Return, found 4 days ago
S$1,158
Return
found 4 days ago
Select Air Canada flight, departing Thu, 5 Mar from Singapore to Chicago, returning Tue, 10 Mar, priced at S$1,158 found 4 days ago
*Available to Expedia members.