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Oak Lawn

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Oak Lawn Flights as Low as $98

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

Frontier Airlines
Tue, Sep 29 - Tue, Oct 6
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$98 Roundtrip, found 2 days ago
$98
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Tue, Sep 29 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Oct 6, priced at $98 found 2 days ago
Frontier Airlines
Sat, Aug 15 - Thu, Sep 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$152 Roundtrip, found 3 days ago
$152
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Sat, Aug 15 from Los Angeles Intl. to O'Hare Intl., returning Thu, Sep 3, priced at $152 found 3 days ago
United
Wed, Jul 1 - Tue, Aug 4
BOS
Logan Intl.
ORD
O'Hare Intl.
$153 Roundtrip, found 3 hours ago
$153
Roundtrip
found 3 hours ago
Select United flight, departing Wed, Jul 1 from Logan Intl. to O'Hare Intl., returning Tue, Aug 4, priced at $153 found 3 hours ago
JetBlue Airways
Wed, Aug 26 - Tue, Sep 15
BOS
Logan Intl.
ORD
O'Hare Intl.
$157 Roundtrip, found 5 days ago
$157
Roundtrip
found 5 days ago
Select JetBlue Airways flight, departing Wed, Aug 26 from Logan Intl. to O'Hare Intl., returning Tue, Sep 15, priced at $157 found 5 days ago
Frontier Airlines
Tue, Jul 7 - Wed, Jul 8
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$162 Roundtrip, found 6 days ago
$162
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Jul 7 from Dallas-Fort Worth Intl. to Midway Intl., returning Wed, Jul 8, priced at $162 found 6 days ago
Delta
Tue, Aug 4 - Thu, Aug 13
BOS
Logan Intl.
ORD
O'Hare Intl.
$179 Roundtrip, found 4 days ago
$179
Roundtrip
found 4 days ago
Select Delta flight, departing Tue, Aug 4 from Logan Intl. to O'Hare Intl., returning Thu, Aug 13, priced at $179 found 4 days ago
American Airlines
Tue, Jun 30 - Tue, Aug 4
BOS
Logan Intl.
RFD
Greater Rockford
$191 Roundtrip, found 20 hours ago
$191
Roundtrip
found 20 hours ago
Select American Airlines flight, departing Tue, Jun 30 from Logan Intl. to Greater Rockford, returning Tue, Aug 4, priced at $191 found 20 hours ago
Frontier Airlines
Tue, Jun 30 - Sat, Jul 4
BOS
Logan Intl.
MDW
Midway Intl.
$260 Roundtrip, found 6 days ago
$260
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Jun 30 from Logan Intl. to Midway Intl., returning Sat, Jul 4, priced at $260 found 6 days ago
Delta
Tue, Jul 21 - Tue, Jul 28
LAX
Los Angeles Intl.
MDW
Midway Intl.
$265 Roundtrip, found 6 days ago
$265
Roundtrip
found 6 days ago
Select Delta flight, departing Tue, Jul 21 from Los Angeles Intl. to Midway Intl., returning Tue, Jul 28, priced at $265 found 6 days ago
Alaska Airlines
Tue, Oct 13 - Sat, Oct 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$291 Roundtrip, found 16 hours ago
$291
Roundtrip
found 16 hours ago
Select Alaska Airlines flight, departing Tue, Oct 13 from Los Angeles Intl. to O'Hare Intl., returning Sat, Oct 17, priced at $291 found 16 hours ago
Delta
Wed, Sep 16 - Sat, Sep 19
DAL
Love Field
ORD
O'Hare Intl.
$292 Roundtrip, found 6 days ago
$292
Roundtrip
found 6 days ago
Select Delta flight, departing Wed, Sep 16 from Love Field to O'Hare Intl., returning Sat, Sep 19, priced at $292 found 6 days ago
American Airlines
Thu, Jan 21 - Tue, Jan 26
DFW
Dallas-Fort Worth Intl.
RFD
Greater Rockford
$307 Roundtrip, found 18 hours ago
$307
Roundtrip
found 18 hours ago
Select American Airlines flight, departing Thu, Jan 21 from Dallas-Fort Worth Intl. to Greater Rockford, returning Tue, Jan 26, priced at $307 found 18 hours ago
American Airlines
Sat, Jul 18 - Sat, Jul 25
LAX
Los Angeles Intl.
RFD
Greater Rockford
$332 Roundtrip, found 6 days ago
$332
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Jul 18 from Los Angeles Intl. to Greater Rockford, returning Sat, Jul 25, priced at $332 found 6 days ago
Contour Airlines
Mon, Sep 28 - Wed, Sep 30
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$334 Roundtrip, found 1 day ago
$334
Roundtrip
found 1 day ago
Select Contour Airlines flight, departing Mon, Sep 28 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Sep 30, priced at $334 found 1 day ago
Delta
Sat, Jun 20 - Tue, Jul 7
DAL
Love Field
MDW
Midway Intl.
$389 Roundtrip, found 15 hours ago
$389
Roundtrip
found 15 hours ago
Select Delta flight, departing Sat, Jun 20 from Love Field to Midway Intl., returning Tue, Jul 7, priced at $389 found 15 hours ago
Sun Country Airlines
Fri, Sep 4 - Sun, Sep 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$498 Roundtrip, found 9 hours ago
$498
Roundtrip
found 9 hours ago
Select Sun Country Airlines flight, departing Fri, Sep 4 from Los Angeles Intl. to O'Hare Intl., returning Sun, Sep 6, priced at $498 found 9 hours ago

Cheap Flights to Oak Lawn

Fall in love at first flight with your vacation to Oak Lawn by saving a ton of cash on your last-minute cheap flight. There’s no more scouring the internet for a good deal—book your flight to Oak Lawn on Hotwire, and you’ll be up, up, and on a getaway in no time.

Because once the wheels are down in Oak Lawn, the good times start rolling. So buckle up, you’re in for a fun ride.

Frequently Asked Questions About flights to Oak Lawn

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Oak Lawn with a tiny bag of pretzels in your hand before you can say “tray tables in the upright position”—and for a ticket price that works for your vacay budget.

So all you have to worry about is where you’re headed after the CHI airport.

What is the cheapest month to fly to Oak Lawn?

Airline ticket prices fluctuate all the time, depending on the day of the week or the month of the year. The cheapest round trip flights to Oak Lawn are in September, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Oak Lawn?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 16 to choose from for your flight to Oak Lawn.

What airport is best to fly into Oak Lawn?

When you’re planning your trip to Oak Lawn, convenience is the name of the game. Luckily, Oak Lawn Midway Intl. Airport is nearby so you can deplane and get going on checking off everything on your Oak Lawn must-do list.

How much are flights to Oak Lawn?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Oak Lawn on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $98, you’ll have leftover cash for at least a magazine and a bottle of water at the airport book store.

How to get cheap flights to Oak Lawn?

The trick to saving a stack of cash on your flight to Oak Lawn? Snatch up that Hotwire flight deal when you see a killer rate because it could be gone in a flash. And with flights as low as $98 right now, why wait?

Oak Lawn Flight Information
Destination airport
O'Hare Intl.
Destination airport IATA code
ORD
Roundtrip price
$118

Last Minute Hotel Deals in Oak Lawn

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
8/10 Very Good! (10,177 reviews)
"We had a clean room, the staff was attentive. It was a great experience!"

Reviewed on Jun 5, 2026

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Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
7.8/10 Good! (1,521 reviews)
"Had a great stay and the staff were excellent and very accommodating. Location is perfect for anyone looking to stay close to the Magnificent Mile. You can park your car and walk to everything. Highly recommend!"

Reviewed on Jun 6, 2026

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The Chicago Hotel Collection - Magnificent Mile
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago ...
9.4/10 Exceptional! (4,358 reviews)
"Excelente atención de todo el personal del hotel. Muy limpio todo, un desayuno super bueno y muy variado. El rooftop con excelente servicio y ofertas, además de vistas increíbles. Excelente ubicación. Definitivamente la cadena hotelera Riu se ha convertido en mi favorita para cualquier destino🤗"

Reviewed on Jun 5, 2026

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Hotel Riu Plaza Chicago
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Book a stay at this business-friendly hotel in Rosemont. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
8.8/10 Excellent! (2,620 reviews)
"Very helpful, polite and nice staff. Clean and confortable rooms. Close to airport."

Reviewed on Jun 5, 2026

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Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (1,551 reviews)
"Everything was good, great location. We walked everywhere, room was clean."

Reviewed on Jun 6, 2026

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The Chicago Hotel Collection Ambassador Gold Coast
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
8/10 Very Good! (3,064 reviews)
"It was a really neat hotel. I liked the style. Wasn't sure why we had to make our own beds though. Also, the phone didn't work in the room, so I tried to call the front desk from my phone. They immediately put me on hold "for a minute", which turned into 5. I hung up to call back thinking they forgot ..."

Reviewed on Jun 6, 2026

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Freehand Chicago
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff in ...
9/10 Wonderful! (2,239 reviews)
"I had an amazing time in Chicago, not one complaint. Everyone was pleasant and my room was clean."

Reviewed on Jun 4, 2026

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Crowne Plaza Chicago West Loop by IHG
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
8.6/10 Excellent! (2,476 reviews)
"Check in was horrible. The longest lines you can imagine….face me 250 Hilton points….not useful for me. Property is beautiful if you look closely but it is not well maintained."

Reviewed on Jun 4, 2026

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Palmer House a Hilton Hotel
See all 4,640 properties in Oak Lawn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Top Hotels With Free Airport Shuttle

Hilton Chicago/Oak Lawn

Hilton Chicago/Oak Lawn

3.5 out of 5
9333 S Cicero Ave Oak Lawn IL
Book a stay at this business-friendly hotel in Oak Lawn. Enjoy free WiFi, breakfast (surcharge), and 24-hour room service. Our guests praise the helpful staff ...
8.4/10 Very Good! (1,348 reviews)
"Very nice and friendly staff"

Reviewed on Jun 4, 2026

Get rates
Hilton Chicago/Oak Lawn
See all 4,640 properties in Oak Lawn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.