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Orland Park

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Orland Park Flights as Low as $89

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

Frontier Airlines
Wed, Jun 3 - Thu, Jun 11
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$89 Roundtrip, found 6 days ago
$89
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Jun 3 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Thu, Jun 11, priced at $89 found 6 days ago
Frontier Airlines
Wed, Sep 16 - Mon, Sep 28
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$89 Roundtrip, found 1 day ago
$89
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Wed, Sep 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Mon, Sep 28, priced at $89 found 1 day ago
Frontier Airlines
Wed, Sep 9 - Tue, Sep 15
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$152 Roundtrip, found 10 hours ago
$152
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Wed, Sep 9 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Sep 15, priced at $152 found 10 hours ago
Frontier Airlines
Tue, Oct 13 - Sat, Oct 17
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$172 Roundtrip, found 7 hours ago
$172
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Tue, Oct 13 from Dallas-Fort Worth Intl. to Midway Intl., returning Sat, Oct 17, priced at $172 found 7 hours ago
Bargain Flight
Wed, Sep 30 - Tue, Oct 6
DCA
Ronald Reagan Washington National
ORD
O'Hare Intl.
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Select Bargain Flight flight, departing Wed, Sep 30 from Ronald Reagan Washington National to O'Hare Intl., returning Tue, Oct 6, priced at $177 found 1 day ago
Bargain Flight
Tue, Nov 3 - Tue, Nov 10
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$178 Roundtrip, found 1 hour ago
$178
Roundtrip
found 1 hour ago
Select Bargain Flight flight, departing Tue, Nov 3 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Tue, Nov 10, priced at $178 found 1 hour ago
American Airlines
Wed, Sep 30 - Tue, Oct 6
DCA
Ronald Reagan Washington National
ORD
O'Hare Intl.
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Select American Airlines flight, departing Wed, Sep 30 from Ronald Reagan Washington National to O'Hare Intl., returning Tue, Oct 6, priced at $197 found 1 day ago
Delta
Wed, Sep 16 - Tue, Sep 29
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 2 hours ago
$197
Roundtrip
found 2 hours ago
Select Delta flight, departing Wed, Sep 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 29, priced at $197 found 2 hours ago
Delta
Tue, Jul 28 - Tue, Aug 11
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$217 Roundtrip, found 14 hours ago
$217
Roundtrip
found 14 hours ago
Select Delta flight, departing Tue, Jul 28 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Tue, Aug 11, priced at $217 found 14 hours ago
Delta
Tue, Jul 21 - Tue, Aug 4
DCA
Ronald Reagan Washington National
MDW
Midway Intl.
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select Delta flight, departing Tue, Jul 21 from Ronald Reagan Washington National to Midway Intl., returning Tue, Aug 4, priced at $217 found 1 day ago
American Airlines
Tue, Jun 23 - Sat, Jun 27
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$276 Roundtrip, found 2 hours ago
$276
Roundtrip
found 2 hours ago
Select American Airlines flight, departing Tue, Jun 23 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Sat, Jun 27, priced at $276 found 2 hours ago
JetBlue Airways
Tue, Aug 4 - Tue, Aug 25
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$297 Roundtrip, found 2 hours ago
$297
Roundtrip
found 2 hours ago
Select JetBlue Airways flight, departing Tue, Aug 4 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Aug 25, priced at $297 found 2 hours ago
Delta
Tue, Oct 13 - Sat, Oct 17
DAL
Love Field
MDW
Midway Intl.
$301 Roundtrip, found 7 hours ago
$301
Roundtrip
found 7 hours ago
Select Delta flight, departing Tue, Oct 13 from Love Field to Midway Intl., returning Sat, Oct 17, priced at $301 found 7 hours ago
Delta
Wed, Sep 9 - Tue, Sep 15
DAL
Love Field
ORD
O'Hare Intl.
$301 Roundtrip, found 10 hours ago
$301
Roundtrip
found 10 hours ago
Select Delta flight, departing Wed, Sep 9 from Love Field to O'Hare Intl., returning Tue, Sep 15, priced at $301 found 10 hours ago
American Airlines
Sun, May 24 - Tue, May 26
DFW
Dallas-Fort Worth Intl.
RFD
Greater Rockford
$378 Roundtrip, found 1 hour ago
$378
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Sun, May 24 from Dallas-Fort Worth Intl. to Greater Rockford, returning Tue, May 26, priced at $378 found 1 hour ago
American Airlines
Tue, May 26 - Tue, Jun 2
BWI
Baltimore Washington Intl. Thurgood Marshall
RFD
Greater Rockford
$622 Roundtrip, found 2 days ago
$622
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, May 26 from Baltimore Washington Intl. Thurgood Marshall to Greater Rockford, returning Tue, Jun 2, priced at $622 found 2 days ago

Cheap Flights to Orland Park

Fall in love at first flight with your vacation to Orland Park 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 Orland Park on Hotwire, and you’ll be up, up, and on a getaway in no time.

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

Frequently Asked Questions About flights to Orland Park

Don’t waste your time on endless searches for cheap airline tickets oneway or roundtrip. We’ll have you on your way to Orland Park 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 Orland Park?

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 Orland Park are in June, but when you book your flight on Hotwire, savings are always in season.

How many airlines fly to Orland Park?

Variety is the spice of life, even when it comes to booking your next trip. Want options for airlines? You’ll find 14 to choose from for your flight to Orland Park.

What airport is best to fly into Orland Park?

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

How much are flights to Orland Park?

Got very cheap flights on your vacation itinerary? When you book your airline tickets to Orland Park on Hotwire, you may just get what’s on your getaway wish list. With tickets as low as $89, 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 Orland Park?

The trick to saving a stack of cash on your flight to Orland Park? 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 $89 right now, why wait?

Orland Park Flight Information
Destination airport
Midway Intl.
Destination airport IATA code
MDW
Roundtrip price
$89

Last Minute Hotel Deals in Orland Park

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! (10,169 reviews)
"This is one of those grand old hotels that used to be amazing, but has now fallen on very hard times. There's a reason it is one of the cheapest (though still expensive) hotels in the Chicago Loop. The staff seemed absent or disinterested, the facility has peeling paint everywhere, and the vibe is ..."

Reviewed on May 20, 2026

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Congress Plaza Hotel
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! (4,195 reviews)
"Extraordinary staff so helpful to my disabled husband. We went to celebrate his birthday in Chicago. I wouldn’t go anywhere else."

Reviewed on May 20, 2026

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Hotel Riu Plaza Chicago
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful ...
8.2/10 Very Good! (2,706 reviews)
"The room was clean but pretty basic. It was good overall but we did have an issue with the a/c switching off in the middle of the night. Unfortunately the hotel didn’t have any fans to remedy that situation. Other than that we had a very enjoyable stay. The location is great!"

Reviewed on May 19, 2026

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Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
8.8/10 Excellent! (5,182 reviews)
"Very pleased with my stay. Room was a little small but otherwise very good. Clean and well maintained. Location is excellent."

Reviewed on May 19, 2026

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River Hotel
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! (3,024 reviews)
"The parking was just across from the hotel. The room was clean. We were surprised how quiet it was even though it was facing a main road. It was also close to the red line which was very convenient."

Reviewed on May 20, 2026

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Freehand Chicago
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2 Chicago IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
8.8/10 Excellent! (2,324 reviews)
"Best service, went above and beyond."

Reviewed on May 20, 2026

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Holiday Inn Chicago Dwtn - The Mart by IHG
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
200 North Columbus Drive Chicago IL
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
8.8/10 Excellent! (2,163 reviews)
"Great breakfast"

Reviewed on May 20, 2026

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Fairmont Chicago at Millennium Park
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario Chicago IL
Stay at this hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the pool and the helpful staff in our reviews. ...
8.6/10 Excellent! (3,236 reviews)
"Valet parking was easy and worth the extra money to be able to take your car in and out of it a few times during your stay. Hotel room had great views on the 18th floor with tall ceilings. Room was clean and had everything I needed and lots of space. The bathroom barn door style was sticking at one ..."

Reviewed on May 20, 2026

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Aloft Chicago Mag Mile
See all 3,405 properties in Orland Park
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.