Cheap flights To Orland Park (CHI) from $29

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Cheap Flights to Orland Park from $29 One Way, $59 Round Trip

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

Mon, Apr 13 - Tue, Apr 14
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$59 Roundtrip, found 23 hours ago
$59
Roundtrip
found 23 hours ago
Select Spirit Airlines flight, departing Mon, Apr 13 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, Apr 14, priced at $59 found 23 hours ago
Tue, Apr 14 - Wed, Apr 22
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$63 Roundtrip, found 2 hours ago
$63
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Tue, Apr 14 from Newark Liberty Intl. Airport to Midway Intl., returning Wed, Apr 22, priced at $63 found 2 hours ago
Tue, May 12 - Tue, May 19
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$67 Roundtrip, found 17 hours ago
$67
Roundtrip
found 17 hours ago
Select Frontier Airlines flight, departing Tue, May 12 from Dallas-Fort Worth Intl. to Midway Intl., returning Tue, May 19, priced at $67 found 17 hours ago
Wed, Apr 22 - Tue, May 5
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$71 Roundtrip, found 13 hours ago
$71
Roundtrip
found 13 hours ago
Select Spirit Airlines flight, departing Wed, Apr 22 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, May 5, priced at $71 found 13 hours ago
Mon, May 11 - Thu, May 14
LGA
LaGuardia
ORD
O'Hare Intl.
$97 Roundtrip, found 1 day ago
$97
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Mon, May 11 from LaGuardia to O'Hare Intl., returning Thu, May 14, priced at $97 found 1 day ago
Tue, Mar 24 - Mon, Mar 30
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$118 Roundtrip, found 1 hour ago
$118
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Tue, Mar 24 from John F. Kennedy Intl. to O'Hare Intl., returning Mon, Mar 30, priced at $118 found 1 hour ago
Wed, Jun 3 - Wed, Jun 10
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$179 Roundtrip, found 6 days ago
$179
Roundtrip
found 6 days ago
Select American Airlines flight, departing Wed, Jun 3 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Jun 10, priced at $179 found 6 days ago
Wed, May 13 - Sat, May 16
LGA
LaGuardia
MDW
Midway Intl.
$181 Roundtrip, found 6 days ago
$181
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, May 13 from LaGuardia to Midway Intl., returning Sat, May 16, priced at $181 found 6 days ago
Tue, Mar 24 - Wed, Mar 25
JFK
John F. Kennedy Intl.
MDW
Midway Intl.
$182 Roundtrip, found 6 days ago
$182
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Tue, Mar 24 from John F. Kennedy Intl. to Midway Intl., returning Wed, Mar 25, priced at $182 found 6 days ago
Mon, Jun 8 - Tue, Jun 9
DAL
Love Field
ORD
O'Hare Intl.
$191 Roundtrip, found 5 days ago
$191
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Mon, Jun 8 from Love Field to O'Hare Intl., returning Tue, Jun 9, priced at $191 found 5 days ago

Orland Park Flight Information

Traveling To
Orland Park
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, American Airlines, Southwest Airlines
Flight Price
$59
Earliest Departing Flight
Latest Departing Flight

Book Your Flight & Hotel Together & Save

Orland Park 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 23 - Apr 25

2 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $543, price is now $366 per person
$366
per person
found 1 day ago
JW Marriott Chicago
4.5-star property

JW Marriott Chicago

Apr 30 - May 2

2 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

Spirit Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $681, price is now $448 per person
$448
per person
found 1 day ago
Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0-star property

Sable at Navy Pier Chicago, Curio Collection by Hilton

Apr 18 - Apr 23

5 night stay

Newark Liberty Intl. Airport (EWR) to Chicago (ORD)

Spirit Airlines • Coach

Chicago (ORD) to Newark Liberty Intl. Airport (EWR)

American Airlines • Coach
Save 100% on your flight
Price was $1,442, price is now $1,018 per person
$1,018
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Newark Liberty Intl. Airport to Orland Park
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Orland Park premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
River Hotel
4.0-star property

River Hotel

8.8/10 Excellent! (5,034 reviews)

Apr 23 - Apr 26

3 night stay

New York (LGA) to Chicago (ORD)

Delta • PremiumEconomy

Chicago (ORD) to New York (LGA)

Spirit Airlines • PremiumEconomy
Price was $742, price is now $689 per person
$689
per person
found 17 hours ago
Very warm atmosphere

Reviewed on Feb 21, 2026

The Peninsula Chicago
5.0-star property

The Peninsula Chicago

9.8/10 Exceptional! (1,003 reviews)

Apr 23 - Apr 26

3 night stay

New York (LGA) to Chicago (ORD)

Delta • PremiumEconomy

Chicago (ORD) to New York (LGA)

Spirit Airlines • PremiumEconomy
Price was $1,692, price is now $1,460 per person
$1,460
per person
found 17 hours ago
Everything was superb. The only “complaint “ I have, is that I paid for a city view room, but actually looked at the side of one building. Other than that, we lived the stay.

Reviewed on Oct 24, 2025

DoubleTree by Hilton Chicago - Magnificent Mile
4.0-star property

DoubleTree by Hilton Chicago - Magnificent Mile

8.8/10 Excellent! (2,357 reviews)

Apr 23 - Apr 26

3 night stay

New York (LGA) to Chicago (ORD)

Delta • PremiumEconomy

Chicago (ORD) to New York (LGA)

Spirit Airlines • PremiumEconomy
Price was $771, price is now $717 per person
$717
per person
found 17 hours ago
clean room, excellent fitness center, great location.

Reviewed on Dec 22, 2025

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See all available trips from New York to Orland Park
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Orland Park

Get the absolute lowest prices on flights to Orland Park 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 Orland Park

Orbitz also provides an array of resources that can help you eliminate most check-in hassles. Detailed baggage information is continually available for Orland Park 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 Orland Park flight using Orbitz.

Frequently asked questions

Which airlines fly to Orland Park?
With 20 airlines to decide from, finding the perfect flight that matches your plans and budget will be a breeze. O'Hare Intl. Airport (ORD) is a major entry point to Orland Park and where you're likely to be flying into. These well-known international carriers will take you there:

  • United Airlines - 612 flights to Orland Park per month
  • American Airlines - 339 flights to Orland Park per month
  • Air Canada - 190 flights to Orland Park per month

What is the best airport to fly to in Orland Park?
Midway Intl. Airport (MDW), around 14 miles northeast of downtown Orland Park, is one choice. O'Hare Intl. Airport (ORD) is another way to get to this city. Compare the fares between the airports, along with which terminal is more convenient for you to touch down at.
How much is a flight to Orland Park?
If you're searching for return flights, airfares fluctuated between $59 and $191 this week. The lowest prices for one-way tickets were $29, departing from New York (EWR).
How to book the cheapest flight to Orland Park?
Using Orbitz, you'll find some of the most incredible flight deals around from a wide selection of airlines. But if you're eager to heighten your chances of picking up cheap flights to Orland Park, here are a few pointers to keep in mind:

  • Departing from or arriving at nearby airports can help you save on airfares. Enter your preferred departure and arrival points. Next, select the 'Nearby airports' function below to look through your options.
  • If your plans aren't carved in stone, click on the 'Show flexible dates' option to scan the flight deals for multiple departure dates. You may find a cheaper fare.
  • To filter your results, hit 'Show options.' You can search based on seating class, airlines, and nonstop and refundable flights. You can also choose the time of day you'd like to fly under 'Sort & Filter' to the left.
  • Once you've settled on your travel dates, reserve your flight. Prices generally rise as the departure date gets closer.
  • Bundle your flights, hotels and car rentals into a competitive package deal. Save your hard-earned money for things you're really excited about, like exploring Orland Park.
  • Don't travel during the busy season if you can. By avoiding summer, school vacations and other popular dates, you can save a significant amount on your airfares.

How long is a flight to Orland Park?
The USA is big, so that depends on where you're departing from. To make things simple, we've chosen some of the main routes to Orland Park and calculated their average flight times:

  • 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 Orland Park?
If your schedule allows, purchase your tickets to Orland Park in January. This is the best month for low airfares, followed by February and August. With a little organizing, you're bound to find a cheap flight with Orbitz.
What day of the week is the cheapest to book a flight to Orland Park?
In general, Tuesdays, Wednesdays and Saturdays are the cheapest days of the week to book flights to Orland Park. If you're looking for the best airfares, search across those days and you could catch a terrific flight deal.
What is the cheapest day of the week to fly to Orland Park?
Look into flying early in the week if you want to score cheap flights to Orland Park. Orbitz data from 2020 shows Monday is normally the cheapest day to set off, followed by Tuesday. Saturdays were shown to have the highest airfares. This is possibly because many travelers choose to start their escape when the working week is over.
What is the cheapest month to fly to Orland Park?
If you're flexible with your travel plans, consider jetting off in August. Orbitz data shows that this is generally the best month to fly out if you're looking for cheap flights to Orland Park. As you might imagine, fares rise in the busy month of June and flights book out quickly.
Which airlines allow free cancellation?
Plans change, and your ticket should be able to as well. That's why Orbitz makes it easy to search for fares with no change fees and free cancellation. Simply enter your departure and arrival points and then click on "Filter by flexible change policies." You can't beat that for peace of mind!
What do I need for the flight to Orland Park?
Flying doesn't have to be a drag. In fact it can be fun if you're well prepared! Make your journey a relaxing one with these handy hints:

  • Your travel documents are the most important things you'll need to carry with you on your flight to Orland Park. To avoid any dramas during check-in, make sure that the personal information on your ticket matches your government-issued ID.
  • Make time fly by even faster on your short hop by packing the right stuff. Think tasty snacks, a water bottle and entertainment. If you want your trip to Orland Park to pass nice and quietly, squeeze some headphones or earplugs in your carry-on bag too.
  • It can get cold on the plane. If you don't like the thought of shivering your way through the flight, wear an extra layer.

How many direct flights are there to Orland Park?
At the moment, there are 604 direct flights every month to Orland Park. When it comes to airlines that will fly you there, you've got plenty to choose from. Southwest Airlines, Frontier Airlines and Delta Air Lines are among the most well-known. Volaris, Porter Airlines and Allegiant Air are some other reputable carriers that offer nonstop services.
How do I get cheap first-class/business deals to Orland Park?
Experienced travelers have a knack for finding business or first-class airfares to Orland Park without the eye-watering price tag. Take their lead with these handy tips:

  • Flexibility isn't just useful in the gym. Avoid locking in your travel dates so you can snap up cheaper airfares when a sale pops up.
  • Low-cost airlines offer business-class seats at a fraction of the usual cost. Skip the full-service carriers and check out these cheaper options.
  • Make a bid for an upgrade. Some carriers hold online auctions that let you offer a price for a seat up the front. You can also try upgrading with points earned through a loyalty program.

How to get into Orland Park from the airport?
Make getting around a breeze with a Midway Intl. Airport (MDW) car rental. Touch down at Midway Intl. Airport (MDW) and then pick up a ride from one of the outlets on-site. Budget and Avis both have a good range of cars to choose from. After you've buckled up, you'll need to drive about 14 miles to the southwest to reach the buzz of central Orland Park. Renting a vehicle from downtown is another option with unbeatable deals available from Orland Park car rentals.
What is the best time to go to Orland Park?
There's no good or bad time to visit Orland Park, but August, September and December are the liveliest months. Like most of the Northern Hemisphere, summertime begins June 20. If you'd like to spend your days in a lightweight top than a winter coat, this time of year may be ideal for you. Expect average daily highs of 80 ºF and nighttime lows around 65 ºF.

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.