Cheap flights To Oak Lawn (CHI) from $50

Earn rewards on top of your airline miles with Orbitz Rewards

Many airlines offer flexible change policies

Sign up to receive text alerts about your trip

Cheap Flights to Oak Lawn from $50 One Way, $146 Round Trip

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

Thu, Aug 6 - Wed, Aug 12
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$146 Roundtrip, found 2 days ago
$146
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Aug 6 from Dallas-Fort Worth Intl. to Midway Intl., returning Wed, Aug 12, priced at $146 found 2 days ago
Wed, Aug 12 - Fri, Aug 14
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$147 Roundtrip, found 2 days ago
$147
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Aug 12 from Dallas-Fort Worth Intl. to Midway Intl., returning Fri, Aug 14, priced at $147 found 2 days ago
Sun, Aug 23 - Thu, Aug 27
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$147 Roundtrip, found 2 days ago
$147
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Aug 23 from Dallas-Fort Worth Intl. to Midway Intl., returning Thu, Aug 27, priced at $147 found 2 days ago
Wed, Oct 21 - Fri, Oct 30
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$154 Roundtrip, found 2 days ago
$154
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Wed, Oct 21 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Fri, Oct 30, priced at $154 found 2 days ago
Wed, Aug 12 - Wed, Aug 12
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$186 Roundtrip, found 4 days ago
$186
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Wed, Aug 12 from John F. Kennedy Intl. to O'Hare Intl., returning Wed, Aug 12, priced at $186 found 4 days ago
Tue, Jul 21 - Tue, Jul 28
EWR
Newark Liberty Intl. Airport
RFD
Greater Rockford
$186 Roundtrip, found 13 hours ago
$186
Roundtrip
found 13 hours ago
Select American Airlines flight, departing Tue, Jul 21 from Newark Liberty Intl. Airport to Greater Rockford, returning Tue, Jul 28, priced at $186 found 13 hours ago
Sat, Sep 26 - Tue, Sep 29
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$187 Roundtrip, found 1 hour ago
$187
Roundtrip
found 1 hour ago
Select United flight, departing Sat, Sep 26 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, Sep 29, priced at $187 found 1 hour ago
Wed, Jul 8 - Wed, Jul 15
JFK
John F. Kennedy Intl.
RFD
Greater Rockford
$191 Roundtrip, found 6 days ago
$191
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Jul 8 from John F. Kennedy Intl. to Greater Rockford, returning Wed, Jul 15, priced at $191 found 6 days ago
Tue, Aug 4 - Tue, Aug 11
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$206 Roundtrip, found 10 hours ago
$206
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Tue, Aug 4 from Los Angeles Intl. to O'Hare Intl., returning Tue, Aug 11, priced at $206 found 10 hours ago
Wed, Aug 5 - Tue, Aug 11
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$222 Roundtrip, found 6 days ago
$222
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Aug 5 from Newark Liberty Intl. Airport to Midway Intl., returning Tue, Aug 11, priced at $222 found 6 days ago

Oak Lawn Flight Information

Traveling To
Oak Lawn
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Frontier Airlines, American Airlines, JetBlue Airways, United, Delta
Flight Price
$146
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 Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

Jul 24 - Jul 27

3 night stay

Baltimore (BWI) to Chicago (ORD)

Frontier Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $1,040, price is now $714 per person
$714
per person
found 1 day ago
Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

Aug 7 - Aug 10

3 night stay

Baltimore (BWI) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Baltimore (BWI)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,285, price is now $898 per person
$898
per person
found 1 day ago
Level Chicago - River North
4.0-star property

Level Chicago - River North

Aug 7 - Aug 10

3 night stay

Baltimore (BWI) to Chicago (ORD)

Southwest Airlines • Coach

Chicago (ORD) to Baltimore (BWI)

Frontier Airlines • Coach
Save 100% on your flight
Price was $1,105, price is now $776 per person
$776
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Baltimore to Oak Lawn
View all trips

Oak Lawn premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown South Loop
3.0-star property

Hilton Garden Inn Chicago Downtown South Loop

8.8/10 Excellent! (2,047 reviews)

Aug 14 - Aug 17

3 night stay

New York (NYC) to Chicago (ORD)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $875, price is now $705 per person
$705
per person
found 10 hours ago
Room was nice, just needed them to vacuum a bit more as someone’s contacts were on the carpet, everything else was good

Reviewed on May 13, 2026

The Langham, Chicago
5.0-star property

The Langham, Chicago

9.8/10 Exceptional! (1,011 reviews)

Aug 14 - Aug 17

3 night stay

New York (NYC) to Chicago (ORD)

JetBlue Airways • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,656, price is now $1,290 per person
$1,290
per person
found 10 hours ago
Just an absolutely beautiful hotel with spectacular service. Highly recommend.

Reviewed on Mar 29, 2024

Nobu Hotel Chicago
5.0-star property

Nobu Hotel Chicago

9.4/10 Exceptional! (869 reviews)

Aug 14 - Aug 17

3 night stay

New York (NYC) to Chicago (ORD)

JetBlue Airways • Roundtrip • PremiumEconomy
Price was $1,380, price is now $1,128 per person
$1,128
per person
found 10 hours ago
The staff was very helpful and courteous. I wish the hotel had more amenities, such as massage services.

Reviewed on May 29, 2026

Don't see what you're looking for?
See all available trips from New York to Oak Lawn
View all trips

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! (4,464 reviews)

Aug 10 - Aug 13

3 night stay

New York (NYC) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,164, price is now $937 per person
$937
per person
found 1 day ago
The room was comfortable and clean. The lobby could stand a refresh.

Reviewed on Jun 19, 2026

Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

9/10 Wonderful! (493 reviews)

Aug 10 - Aug 13

3 night stay

New York (NYC) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,445, price is now $1,119 per person
$1,119
per person
found 1 day ago
We always love staying here. Such great service and nice accommodations.

Reviewed on Nov 20, 2025

Grand Geneva Resort & Spa
4.0-star property

Grand Geneva Resort & Spa

8.8/10 Excellent! (1,010 reviews)

Aug 10 - Aug 13

3 night stay

New York (NYC) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,449, price is now $1,145 per person
$1,145
per person
found 1 day ago
Beautiful property and nice staff

Reviewed on Apr 13, 2026

Don't see what you're looking for?
See all available trips from New York to Oak Lawn
View all trips

Oak Lawn

When you plan to buy tickets for flights to Oak Lawn, you don’t have to look any further than Orbitz! We offer bargain rates and low fares on thousands of flights.

Reliable Customer Service

Along with our low prices, Orbitz is well known for exceptional customer care. We make it simple to find the best Oak Lawn flights for you. If you need to cancel your booking or change your flight plans, simply contact our Customer Service department to make any adjustments.

Bargain Tickets for Oak Lawn Flights

Orbitz offers deeply discounted flights to Oak Lawn, and we provide the resources to research your travel destination and plan your complete itinerary.

Use Orbitz to Earn Points with Your Frequent Flyer Program

Saving your frequent flyer miles for your flights to Oak Lawn? You can use Orbitz to make your budget ticket reservation for all your flights and still earn points or miles on your frequent flyer program! Just enter your program account number while you’re booking your ticket to have your points added automatically, every time you book with Orbitz.

Convenient Travel Planning Services

If you like the ease of making your travel plans on the move, you’ll love the free Orbitz apps for iPhones, iPads, and Android devices. You can use these apps to review your travel reservations or make a change to your itinerary. Orbitz also offers additional travel assistance such as free mobile alerts that keep you up-to-date about sudden changes to your upcoming flights. You can also browse Orbitz easily on your smartphone by using the mobile version of the website to find budget Oak Lawn flights.

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 $146 to $222. But it was passengers beginning their trip from Dallas (DFW) who nabbed the biggest bargains. One-way flights to Oak Lawn fell to just $50.
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.