Cheap flights To Oak Lawn (CHI) from $29

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Cheap Flights to Oak Lawn from $29 One Way, $58 Round Trip

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

Tue, Mar 10 - Wed, Mar 11
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$58 Roundtrip, found 1 day ago
$58
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Mar 10 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Mar 11, priced at $58 found 1 day ago
Sat, Feb 14 - Sat, Feb 21
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$59 Roundtrip, found 14 hours ago
$59
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Sat, Feb 14 from Dallas-Fort Worth Intl. to Midway Intl., returning Sat, Feb 21, priced at $59 found 14 hours ago
Thu, Jan 15 - Sun, Jan 18
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$59 Roundtrip, just found
$59
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Jan 15 from Newark Liberty Intl. Airport to Midway Intl., returning Sun, Jan 18, priced at $59 just found
Fri, Jan 23 - Sat, Jan 24
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$72 Roundtrip, just found
$72
Roundtrip
just found
Select Spirit Airlines flight, departing Fri, Jan 23 from Newark Liberty Intl. Airport to O'Hare Intl., returning Sat, Jan 24, priced at $72 just found
Thu, Apr 9 - Mon, Apr 13
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$101 Roundtrip, found 4 days ago
$101
Roundtrip
found 4 days ago
Select Sun Country Airlines flight, departing Thu, Apr 9 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Mon, Apr 13, priced at $101 found 4 days ago
Sat, Jan 3 - Sat, Jan 10
BOS
Logan Intl.
MDW
Midway Intl.
$124 Roundtrip, found 5 days ago
$124
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Sat, Jan 3 from Logan Intl. to Midway Intl., returning Sat, Jan 10, priced at $124 found 5 days ago
Sat, Feb 7 - Tue, Feb 10
BOS
Logan Intl.
ORD
O'Hare Intl.
$127 Roundtrip, found 1 day ago
$127
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Sat, Feb 7 from Logan Intl. to O'Hare Intl., returning Tue, Feb 10, priced at $127 found 1 day ago
Tue, Jan 13 - Tue, Jan 20
BOS
Logan Intl.
ORD
O'Hare Intl.
$132 Roundtrip, found 1 day ago
$132
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Jan 13 from Logan Intl. to O'Hare Intl., returning Tue, Jan 20, priced at $132 found 1 day ago
Sat, Feb 7 - Sat, Feb 14
BOS
Logan Intl.
ORD
O'Hare Intl.
$134 Roundtrip, found 17 hours ago
$134
Roundtrip
found 17 hours ago
Select JetBlue Airways flight, departing Sat, Feb 7 from Logan Intl. to O'Hare Intl., returning Sat, Feb 14, priced at $134 found 17 hours ago
Thu, Jan 15 - Sat, Jan 17
BOS
Logan Intl.
ORD
O'Hare Intl.
$135 Roundtrip, found 2 days ago
$135
Roundtrip
found 2 days ago
Select United flight, departing Thu, Jan 15 from Logan Intl. to O'Hare Intl., returning Sat, Jan 17, priced at $135 found 2 days ago

Oak Lawn Flight Information

Traveling To
Oak Lawn
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, Sun Country Airlines, Southwest Airlines, JetBlue Airways, United, American Airlines
Flight Price
$58
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.
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Jan 29 - Jan 31

2 night stay

Atlanta (ATL) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Price was $300, price is now $210 per person
$210
per person
found 1 day ago
Hotel Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

Feb 4 - Feb 8

4 night stay

Atlanta (ATL) to Chicago (ORD)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $343, price is now $239 per person
$239
per person
found 1 day ago
Swissotel - Chicago
4.5-star property

Swissotel - Chicago

Feb 4 - Feb 8

4 night stay

Atlanta (ATL) to Chicago (ORD)

Spirit Airlines • Non-stop roundtrip • Coach
Save 100% on your flight
Price was $398, price is now $279 per person
$279
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.
Springhill Suites by Marriott Chicago Downtown/ River North
3.5-star property

Springhill Suites by Marriott Chicago Downtown/ River North

9.2/10 Wonderful! (1,006 reviews)

Feb 19 - Feb 22

3 night stay

San Juan (SJU) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $827, price is now $723 per person
$723
per person
found 1 day ago
Great location and friendly staff.

Reviewed on May 14, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,790 reviews)

Feb 19 - Feb 22

3 night stay

San Juan (SJU) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $932, price is now $777 per person
$777
per person
found 1 day ago
Enjoyed our stay in Chicago...coldest weekend ever, but the accommodations were tip-top. Room was clean and well appointed. Staff was incredibly attentive and responsive. The breakfast buffet was very good and a great value for this well located hotel.

Reviewed on Dec 15, 2025

Hilton Chicago O'Hare Airport
4.0-star property

Hilton Chicago O'Hare Airport

8.2/10 Very Good! (2,158 reviews)

Feb 19 - Feb 22

3 night stay

San Juan (SJU) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,043, price is now $909 per person
$909
per person
found 1 day ago
Awesome hotel, an island of peace and calm and first class treatment in a sea of chaos at O'Hare airport. Staff, restaurant, services--worth every penny. Early departure? Stay here the night before. We did. Calmly woke up and walked to the terminal thru the underground walkways. Truly pleasant and memorable stay.

Reviewed on Nov 11, 2025

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Oak Lawn first class flight packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago Schaumburg
4.0-star property

DoubleTree by Hilton Chicago Schaumburg

7.2/10 Good! (1,003 reviews)

Feb 18 - Feb 22

4 night stay

Boston (BOS) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $739, price is now $676 per person
$676
per person
just found
Great property, phenomenal experience

Reviewed on Oct 6, 2025

Hilton Chicago O'Hare Airport
4.0-star property

Hilton Chicago O'Hare Airport

8.2/10 Very Good! (2,158 reviews)

Feb 18 - Feb 22

4 night stay

Boston (BOS) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,141, price is now $959 per person
$959
per person
just found
Awesome hotel, an island of peace and calm and first class treatment in a sea of chaos at O'Hare airport. Staff, restaurant, services--worth every penny. Early departure? Stay here the night before. We did. Calmly woke up and walked to the terminal thru the underground walkways. Truly pleasant and memorable stay.

Reviewed on Nov 11, 2025

Hilton Rosemont Chicago O'Hare
3.5-star property

Hilton Rosemont Chicago O'Hare

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

Feb 18 - Feb 22

4 night stay

Boston (BOS) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $915, price is now $834 per person
$834
per person
just found
Good hotel close to airport, with free airport shuttle, 7-10 min away. Quite convenient

Reviewed on Nov 4, 2025

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Oak Lawn

Get the absolute lowest prices on flights to Oak Lawn by shopping with Orbitz. Orbitz is the most efficient travel planner around, allowing you to search, compare and book discount domestic and international flights fast. With cutting-edge mobile tools and access to frequent flier rewards programs, we have everything you need for both your routine and holiday excursions.

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Avoid Check-In Hassles When Traveling On Flights to Oak Lawn

Orbitz also provides an array of resources that can help you eliminate most check-in hassles. Detailed baggage information is continually available for Oak Lawn flights. Mobile apps can also be used to share travel itineraries with family members or business associates.

Keeping Everyone Up To Date

When you download the free Orbitz mobile phone app, you can get regular and free flight updates. These will keep you informed of important scheduling changes. Updates can even be sent to several contacts, helping to keep everyone current on anticipated arrival times and all other relevant flight details.

Orbitz makes traveling on a budget very easy to do. We provide everything you need to plan your ideal trip from start to finish. Getting there and back again is a snap when you book your Oak Lawn flight using Orbitz.

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 $58 to $135. But it was passengers beginning their trip from Dallas (DFW) who nabbed the biggest bargains. One-way flights to Oak Lawn fell to just $29.
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.