Cheap flights To Oak Lawn (CHI) from $28

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Cheap Flights to Oak Lawn from $28 One Way, $57 Round Trip

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

Wed, Apr 15 - Tue, Apr 21
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$57 Roundtrip, found 21 hours ago
$57
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Wed, Apr 15 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Apr 21, priced at $57 found 21 hours ago
Tue, May 5 - Wed, May 13
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$57 Roundtrip, found 12 hours ago
$57
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Tue, May 5 from Dallas-Fort Worth Intl. to Midway Intl., returning Wed, May 13, priced at $57 found 12 hours ago
Wed, Apr 22 - Wed, Apr 29
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$57 Roundtrip, found 3 hours ago
$57
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Wed, Apr 22 from Newark Liberty Intl. Airport to Midway Intl., returning Wed, Apr 29, priced at $57 found 3 hours ago
Thu, Apr 9 - Tue, Apr 14
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$87 Roundtrip, found 1 day ago
$87
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Apr 9 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, Apr 14, priced at $87 found 1 day ago
Thu, Jun 4 - Thu, Jun 11
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$95 Roundtrip, found 2 hours ago
$95
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Thu, Jun 4 from Los Angeles Intl. to O'Hare Intl., returning Thu, Jun 11, priced at $95 found 2 hours ago
Wed, Apr 8 - Tue, Apr 21
LGA
LaGuardia
ORD
O'Hare Intl.
$103 Roundtrip, found 6 hours ago
$103
Roundtrip
found 6 hours ago
Select Spirit Airlines flight, departing Wed, Apr 8 from LaGuardia to O'Hare Intl., returning Tue, Apr 21, priced at $103 found 6 hours ago
Wed, Apr 22 - Wed, Apr 29
LGA
LaGuardia
MDW
Midway Intl.
$144 Roundtrip, found 3 hours ago
$144
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Wed, Apr 22 from LaGuardia to Midway Intl., returning Wed, Apr 29, priced at $144 found 3 hours ago
Tue, Jun 2 - Wed, Jun 3
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$162 Roundtrip, found 11 hours ago
$162
Roundtrip
found 11 hours ago
Select United flight, departing Tue, Jun 2 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, Jun 3, priced at $162 found 11 hours ago
Tue, Jun 2 - Wed, Jun 3
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$162 Roundtrip, found 11 hours ago
$162
Roundtrip
found 11 hours ago
Select American Airlines flight, departing Tue, Jun 2 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, Jun 3, priced at $162 found 11 hours ago
Thu, Apr 23 - Sat, Apr 25
LGA
LaGuardia
MDW
Midway Intl.
$163 Roundtrip, found 14 hours ago
$163
Roundtrip
found 14 hours ago
Select Southwest Airlines flight, departing Thu, Apr 23 from LaGuardia to Midway Intl., returning Sat, Apr 25, priced at $163 found 14 hours ago

Oak Lawn Flight Information

Traveling To
Oak Lawn
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, American Airlines, Southwest Airlines, United
Flight Price
$57
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Oak Lawn economy 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

Apr 29 - May 1

2 night stay

Denver (DEN) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to Denver (DEN)

Southwest Airlines • Coach
Price was $480, price is now $354 per person
$354
per person
found 1 day ago
Fairmont Chicago at Millennium Park
4.5-star property

Fairmont Chicago at Millennium Park

Apr 30 - May 3

3 night stay

Denver (DEN) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Denver (DEN)

Frontier Airlines • Coach
Save 100% on your flight
Price was $940, price is now $690 per person
$690
per person
found 12 hours ago
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

May 6 - May 11

5 night stay

Denver (DEN) to Chicago (ORD)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $2,154, price is now $1,637 per person
$1,637
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.
Holiday Inn Express & Suites Chicago - Oak Forest by IHG
2.5-star property

Holiday Inn Express & Suites Chicago - Oak Forest by IHG

9/10 Wonderful! (533 reviews)

May 8 - May 10

2 night stay

San Francisco (SFO) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $853, price is now $803 per person
$803
per person
found 1 day ago
Very clean rooms and building. Staff is the best. Theo, Bri and Toi are so accomadating

Reviewed on Jan 17, 2026

Home2 Suites by Hilton Hammond
3.0-star property

Home2 Suites by Hilton Hammond

8.4/10 Very Good! (286 reviews)

May 7 - May 10

3 night stay

San Francisco (SFO) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $848, price is now $829 per person
$829
per person
found 8 hours ago
Friendly staff . Clean , quiet , comfortable .

Reviewed on Jun 13, 2024

Hilton Garden Inn Merrillville
3.0-star property

Hilton Garden Inn Merrillville

8.4/10 Very Good! (1,000 reviews)

May 8 - May 10

2 night stay

San Francisco (SFO) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $858, price is now $836 per person
$836
per person
found 1 day ago
Would definitely stay here again. Perfect overnight stop on a long road trip.

Reviewed on Nov 22, 2025

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Oak Lawn first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

8.2/10 Very Good! (2,582 reviews)

May 16 - May 18

2 night stay

New York (LGA) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,231, price is now $1,051 per person
$1,051
per person
found 17 hours ago
The rooms were clean and smelled fresh.

Reviewed on Jan 8, 2026

Level Chicago - River North
4.0-star property

Level Chicago - River North

9.2/10 Wonderful! (876 reviews)

May 16 - May 18

2 night stay

New York (LGA) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,237, price is now $1,115 per person
$1,115
per person
found 17 hours ago
The pool area is fantastic. Rooms very ample-sized and comfortable. I would stay here again!

Reviewed on Jul 8, 2024

Sports Illustrated Resorts Chicago
4.5-star property

Sports Illustrated Resorts Chicago

9.2/10 Wonderful! (1,414 reviews)

May 16 - May 18

2 night stay

New York (LGA) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,330, price is now $1,211 per person
$1,211
per person
found 17 hours ago
The location was great and made it easy to navigate about the city. The staff were all extremely friendly and helpful, and the perks of staying here were great. They offered a complimentary item from the coffee shop and hosted happy hour during my stay. My room was neat and well kept and a great place for me to land.

Reviewed on Jan 20, 2026

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Oak Lawn

Why search for low cost fares on your flights to Oak Lawn when Orbitz offers the guaranteed lowest prices on foreign and domestic flights? When you travel with Orbitz you can benefit from:

Bargain Flights to Oak Lawn

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Orbitz sends you free alerts and updates on your Oak Lawn flight wherever you are in the world. Once you have downloaded the free app for your iPhone, Android, or iPad, you can review or alter any travel plans that you have made or even book a future flight for business or pleasure. If you need to reserve a hotel room when booking your flight, you will find exclusive deals on our mobile site.

Frequent Flyer Program Enrolment

Orbitz finds you the lowest fares, but you can still add your miles to your frequent flyer program to earn miles or points on selected flights to Oak Lawn. When making your booking, reference your frequent flyer number to receive discounts in the future.

Outstanding Customer Service

Orbitz values your business and wants to ensure that all of your flights are as easy as possible to book. If you have booked a flight to Oak Lawn but need to cancel it, you may be able to do so online. If you have any questions or need help, the dedicated Orbitz customer service team is always standing by.

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 $57 to $163. But it was passengers beginning their trip from Dallas (DFW) who nabbed the biggest bargains. One-way flights to Oak Lawn fell to just $28.
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.