Cheap flights To Oak Lawn (CHI) from $25

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Cheap Flights to Oak Lawn from $25 One Way, $49 Round Trip

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Sat, Nov 8 - Sat, Nov 15
LGA
LaGuardia
ORD
O'Hare Intl.
$49 Roundtrip, found 2 hours ago
$49
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Sat, Nov 8 from LaGuardia to O'Hare Intl., returning Sat, Nov 15, priced at $49 found 2 hours ago
Wed, Nov 12 - Wed, Nov 12
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$51 Roundtrip, found 16 hours ago
$51
Roundtrip
found 16 hours ago
Select Spirit Airlines flight, departing Wed, Nov 12 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Nov 12, priced at $51 found 16 hours ago
Thu, Dec 4 - Thu, Dec 4
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$64 Roundtrip, found 2 days ago
$64
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Dec 4 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Thu, Dec 4, priced at $64 found 2 days ago
Sat, Dec 6 - Sat, Dec 6
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$64 Roundtrip, found 2 hours ago
$64
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Sat, Dec 6 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Dec 6, priced at $64 found 2 hours ago
Mon, Dec 15 - Mon, Dec 15
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$64 Roundtrip, found 18 hours ago
$64
Roundtrip
found 18 hours ago
Select Frontier Airlines flight, departing Mon, Dec 15 from Dallas-Fort Worth Intl. to Midway Intl., returning Mon, Dec 15, priced at $64 found 18 hours ago
Tue, Nov 11 - Thu, Nov 13
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$64 Roundtrip, found 4 hours ago
$64
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Tue, Nov 11 from Newark Liberty Intl. Airport to Midway Intl., returning Thu, Nov 13, priced at $64 found 4 hours ago
Wed, Nov 5 - Wed, Nov 12
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$87 Roundtrip, just found
$87
Roundtrip
just found
Select Spirit Airlines flight, departing Wed, Nov 5 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, Nov 12, priced at $87 just found
Tue, Dec 9 - Sat, Dec 13
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$101 Roundtrip, found 1 day ago
$101
Roundtrip
found 1 day ago
Select United flight, departing Tue, Dec 9 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Dec 13, priced at $101 found 1 day ago
Tue, Dec 9 - Sat, Dec 13
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$101 Roundtrip, found 1 day ago
$101
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Dec 9 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, Dec 13, priced at $101 found 1 day ago
Thu, Jan 8 - Thu, Jan 15
DAL
Love Field
MDW
Midway Intl.
$109 Roundtrip, found 4 days ago
$109
Roundtrip
found 4 days ago
Select Southwest Airlines flight, departing Thu, Jan 8 from Love Field to Midway Intl., returning Thu, Jan 15, priced at $109 found 4 days ago

Oak Lawn Flight Information

Traveling To
Oak Lawn
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Spirit Airlines, Frontier Airlines, American Airlines, Southwest Airlines, United
Flight Price
$49
Earliest Departing Flight
Latest Departing Flight

Flights Review

Mar 10, 2018

Great overall service. Smooth landing. Plane was even early.

A verified traveler
Denver to Chicago · United

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Oak Lawn economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago Downtown
4.0-star property

The Royal Sonesta Chicago Downtown

Dec 13 - Dec 16

3 night stay

Detroit (DTW) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
Price was $370, price is now $233 per person
$233
per person
found 1 day ago
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Dec 13 - Dec 16

3 night stay

Detroit (DTW) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
Price was $470, price is now $278 per person
$278
per person
found 1 day ago
Fairmont Chicago at Millennium Park
4.5-star property

Fairmont Chicago at Millennium Park

Dec 13 - Dec 16

3 night stay

Detroit (DTW) to Chicago (ORD)

United • Roundtrip • Coach
Save 100% on your flight
Price was $434, price is now $287 per person
$287
per person
found 1 day ago
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Oak Lawn premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago O'Hare Airport
4.0-star property

Hilton Chicago O'Hare Airport

8.2/10 Very Good! (2,141 reviews)

Nov 25 - Nov 28

3 night stay

Minneapolis (MSP) to Chicago (ORD)

Delta • Roundtrip • PremiumEconomy
Price was $938, price is now $706 per person
$706
per person
found 19 hours ago
The AC was not working properly and the room felt stuffy. We were there for a night and could not sleep after a couple of hours because of stuffiness.

Reviewed on Sep 14, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,761 reviews)

Nov 25 - Nov 28

3 night stay

Minneapolis (MSP) to Chicago (ORD)

Delta • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,421, price is now $1,034 per person
$1,034
per person
found 19 hours ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!

Reviewed on Oct 13, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile
3.5-star property

Hilton Grand Vacations Club Chicago Magnificent Mile

9.2/10 Wonderful! (303 reviews)

Nov 25 - Nov 28

3 night stay

Minneapolis (MSP) to Chicago (ORD)

Delta • Roundtrip • PremiumEconomy
Price was $954, price is now $778 per person
$778
per person
found 19 hours ago
close to everything we will be staying here again on our next vacation to Chicago

Reviewed on Aug 31, 2024

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Oak Lawn first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,602 reviews)

Nov 26 - Dec 3

7 night stay

Seattle (SEA) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $2,649, price is now $1,509 per person
$1,509
per person
found 1 day ago
One day didn’t receive room service

Reviewed on Sep 2, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,761 reviews)

Nov 26 - Dec 3

7 night stay

Seattle (SEA) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $3,449, price is now $2,128 per person
$2,128
per person
found 1 day ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!

Reviewed on Oct 13, 2025

Waldorf Astoria Chicago
5.0-star property

Waldorf Astoria Chicago

9.4/10 Exceptional! (1,004 reviews)

Nov 26 - Dec 3

7 night stay

Seattle (SEA) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $3,732, price is now $2,449 per person
$2,449
per person
found 1 day ago
Front desk staff was very attentive! We celebrated my sisters 30th birthday and they upgraded our room!

Reviewed on Feb 13, 2023

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Oak Lawn

If you are looking for affordable flights to Oak Lawn, look no further. Orbitz offers discounted rates to many destinations.

Bargain flights to Oak Lawn now available

As you review your budget and travel plans, consider the low fares Orbitz offers on Oak Lawn flights. With Orbitz, booking flights to Oak Lawn is easy and the lowest prices are guaranteed.

Easy self-help service offered

Orbitz offers cutting edge mobile tools that allow you to review and make bookings from your Android or iPhone mobile device with a simple application. You can easily and conveniently update your information or book your trip using this service. You are also able to obtain information on affordable hotel packages and receive frequent flight updates. You will receive confirmation of bookings or reservations made using the mobile service on the same day of the request. Change details or receive updates on your Oak Lawn flights by visiting the Orbitz site or mobile application.

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Orbitz ensures that you are kept informed with up-to-date flight information, providing feedback to up to six contact numbers to ensure that everyone receives the feedback. In addition to providing the discounted deals on Oak Lawn flights, Orbitz is also able to structure a package based on your needs for activities, car hire and accommodations.

Traveler profile updates

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Frequently asked questions

Which airlines fly to Oak Lawn?
With 20 airlines to pick from, finding the ideal flight that fits your budget and plans will be easy. O'Hare Intl. Airport (ORD) is a major entrance point to Oak Lawn and where you'll likely be flying into. These well-known international carriers are ready to take you there:

  • United Airlines - 612 flights to Oak Lawn per month
  • American Airlines - 339 flights to Oak Lawn per month
  • Air Canada - 190 flights to Oak Lawn per month

What is the best airport to fly to in Oak Lawn?
Midway Intl. Airport (MDW), around 5 miles north of downtown Oak Lawn, is one choice. O'Hare Intl. Airport (ORD) is another port of entry to this exciting city. Compare the airfares to both airports, as well as which terminal may be more convenient for you.
How much is a flight to Oak Lawn?
Plenty of great deals were there for the taking this week, with return flights to Oak Lawn fluctuating from $49 to $109. But it was passengers beginning their trip from New York (LGA) who nabbed the biggest bargains. One-way flights to Oak Lawn fell to just $25.
How to book the cheapest flight to Oak Lawn?
With some of the most incredible flight deals around, a bargain is always waiting for you with Orbitz. The following tips and hints will help you land cheap flights to Oak Lawn — and leave you with more cash to splash:

  • Depending on your departure city, select the 'Nearby airports' function (located under the departure and arrival options). On occasion, alternative departure points offer better value for money.
  • If you're flexible with your plans, click on the 'Show flexible dates' option. You'll see the flight deals for the days either side of your selected departure. Airfares often vary depending on what day it is.
  • Select 'Show options' to filter your search results. You can pick your preferred seating class and airline here. Under 'Sort & Filter' to the left, you can even specify whether you'd like to fly in the morning, afternoon or evening.
  • Reserve your seat as soon as you've decided on your travel dates. While you can get lucky once in a while, airline tickets rarely drop in price as your departure date nears.
  • Think about bundling your hotels, flights and car rental with Orbitz to make your dollar go further.
  • If you can, avoid traveling during the busy season. Airfares significantly increase during summer, school breaks and around other vacation times like Easter, Thanksgiving and Christmas.

How long is a flight to Oak Lawn?
You might have time to read one or more chapters of your favorite novel, or you might get through the whole thing! How long a flight is depends on where you're taking off from, but these well-known routes to Oak Lawn will give you some idea:

  • New York, NY (LGA-LaGuardia) to O'Hare Intl. Airport (ORD) - 2 hours and 40 minutes
  • Boston, MA (BOS-Logan Intl.) to O'Hare Intl. Airport (ORD) - 2 hours and 51 minutes
  • Washington, DC (DCA-Ronald Reagan Washington National) to O'Hare Intl. Airport (ORD) - 2 hours and 13 minutes

What is the best time to book a flight to Oak Lawn?
Book in January, February or August for the lowest airfares to Oak Lawn. Once you've located a bargain, buy it — cheap flights are known to appear and then vanish in the click of a mouse.
What day of the week is the cheapest to book a flight to Oak Lawn?
Get a great flight deal by booking on a Tuesday, Wednesday or Saturday. These are typically the best days of the week to land cheap airfares to Oak Lawn.
What is the cheapest day of the week to fly to Oak Lawn?
Based on Orbitz data from 2020, Monday is generally the best day to get cheap flights to Oak Lawn. Tuesday also offers more affordable fares, whereas Saturday has the most expensive ticket prices. Although flying out at the weekend can be more suitable, you'll have more money to play with if you jet out early in the week.
What is the cheapest month to fly to Oak Lawn?
We won't keep you guessing — according to Orbitz data, August is generally the cheapest month to fly. Ideal for those who need a weekend getaway or simply escape from it all before the weather changes. The costliest time to fly is in the middle of summer, with airfares peaking in June.
Which airlines allow free cancellation?
We understand that plans can change and flexibility is important. That's why you can easily search for flights that include free cancellation and no change fees on Orbitz. Simply click on "Filter by flexible change policies" and we'll show you fares more flexible than a crayon left in the sun!
What do I need for the flight to Oak Lawn?
Nothing's more enjoyable than jetting somewhere new, but it's wise to be prepared. These practical tips will help get your trip off to a smooth start:

  • Whether you print it out beforehand or use an electronic one, you'll need your boarding pass to walk on to the plane. You'll also need some sort of government-issued photo identification. If you're flying internationally, make sure your passport is valid and you've looked into visa requirements.
  • Take some activities to keep you amused on your trip to Oak Lawn. Magazines, books and electronic gadgets like laptops and tablets should do the trick. Remember to take a water bottle as well. Even on short flights, it's important to stay hydrated.
  • Even if you're traveling when it's hot and sticky outside, take a sweater or cardigan on board with you. Cabins can get chilly!

How many direct flights are there to Oak Lawn?
Right now, there are 604 direct flights every month to Oak Lawn. When it comes to airlines that will take you there, you're spoiled for choice. Southwest Airlines, Frontier Airlines and Delta Air Lines are among the most popular. Volaris, Porter Airlines and Allegiant Air are other respected carriers with nonstop services.
How do I get cheap first-class/business deals to Oak Lawn?
If you think a first or business-class fare is out of your reach, think again. Here are some terrific tips to help you pick up a premium flight to Oak Lawn for a whole lot less:

  • Be more flexible with your travel dates and hold out for deals on first or business-class airfares.
  • Search for a budget carrier that offers business-class seats. They usually come with extra legroom and a glass of Champagne — and a more attractive price.
  • Bid for an upgrade in online auctions (if available) or upgrade your fare with points earned through loyalty programs.

How to get into Oak Lawn from the airport?
Zip into central Oak Lawn with a Midway Intl. Airport (MDW) car rental. Budget and Avis are two reputable providers at Midway Intl. Airport (MDW). Fling your bags in the trunk, drive 5 miles to the south and you'll be in the center of the city in a jiffy. Many travelers also use taxis or public transportation to head into town from the airport. From there, you can still pick up a ride to see the region's other great attractions with one of our Oak Lawn car rentals.
What is the best time to go to Oak Lawn?
You'll have plenty of fun whatever time of the year you decide to go to Oak Lawn, but March, April and May are the liveliest months. Like to fill up your schedule with loads of warm-weather experiences? Book your trip around June 20. This is when the summer season kicks off in the Northern Hemisphere. Expect the mercury to span between 65 ºF and 80 ºF at this time of year.
Travel tips for Oak Lawn

  • Downtown Oak Lawn is brimming with interesting attractions. Gems like Chicago Ridge Shopping Mall and Childrens Museum of Oak Lawn will keep your feet moving and the sightseer in you happy.
  • If you're looking for a nice little day trip, there are more sights to see a short drive from the center. Discover why Wrigley Field and McCormick Place are on the must-do lists of many Oak Lawn visitors.
  • When you want to see more of Chicago, lock in a car rental and drive in the direction of Gurnee. Waukegan is another main city with no shortage of things to see and do.

More to Explore

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.