Cheap flights To Oak Brook (CHI) from $28

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Cheap Flights to Oak Brook from $28 One Way, $56 Round Trip

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

Wed, Mar 25 - Mon, Mar 30
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$56 Roundtrip, found 2 hours ago
$56
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Mar 25 from John F. Kennedy Intl. to O'Hare Intl., returning Mon, Mar 30, priced at $56 found 2 hours ago
Wed, May 6 - Sat, May 9
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$56 Roundtrip, found 3 hours ago
$56
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Wed, May 6 from Newark Liberty Intl. Airport to Midway Intl., returning Sat, May 9, priced at $56 found 3 hours ago
Sat, Apr 25 - Mon, May 4
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$57 Roundtrip, just found
$57
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Apr 25 from Newark Liberty Intl. Airport to Midway Intl., returning Mon, May 4, priced at $57 just found
Tue, Mar 17 - Tue, Mar 24
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$58 Roundtrip, just found
$58
Roundtrip
just found
Select Spirit Airlines flight, departing Tue, Mar 17 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, Mar 24, priced at $58 just found
Tue, Mar 17 - Sun, Mar 29
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$61 Roundtrip, found 1 day ago
$61
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Tue, Mar 17 from John F. Kennedy Intl. to O'Hare Intl., returning Sun, Mar 29, priced at $61 found 1 day ago
Sat, Apr 25 - Mon, May 4
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$65 Roundtrip, just found
$65
Roundtrip
just found
Select Spirit Airlines flight, departing Sat, Apr 25 from Newark Liberty Intl. Airport to O'Hare Intl., returning Mon, May 4, priced at $65 just found
Wed, Mar 25 - Mon, Mar 30
LGA
LaGuardia
ORD
O'Hare Intl.
$74 Roundtrip, found 2 hours ago
$74
Roundtrip
found 2 hours ago
Select Spirit Airlines flight, departing Wed, Mar 25 from LaGuardia to O'Hare Intl., returning Mon, Mar 30, priced at $74 found 2 hours ago
Sat, May 2 - Sat, May 9
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$88 Roundtrip, just found
$88
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, May 2 from Los Angeles Intl. to O'Hare Intl., returning Sat, May 9, priced at $88 just found
Thu, Apr 30 - Thu, Apr 30
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$142 Roundtrip, found 7 hours ago
$142
Roundtrip
found 7 hours ago
Select JetBlue Airways flight, departing Thu, Apr 30 from John F. Kennedy Intl. to O'Hare Intl., returning Thu, Apr 30, priced at $142 found 7 hours ago
Sat, May 2 - Tue, May 5
LGA
LaGuardia
RFD
Greater Rockford
$147 Roundtrip, found 1 day ago
$147
Roundtrip
found 1 day ago
Select American Airlines flight, departing Sat, May 2 from LaGuardia to Greater Rockford, returning Tue, May 5, priced at $147 found 1 day ago

Oak Brook Flight Information

Traveling To
Oak Brook
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, Southwest Airlines, JetBlue Airways, American Airlines
Flight Price
$56
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

Book Your Flight & Hotel Together & Save

Oak Brook 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 19 - Apr 21

2 night stay

Boston (BOS) to Chicago (ORD)

Frontier Airlines • Non-stop • Coach

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Non-stop • Coach
Price was $470, price is now $295 per person
$295
per person
found 1 day ago
JW Marriott Chicago
4.5-star property

JW Marriott Chicago

Apr 19 - Apr 21

2 night stay

Boston (BOS) to Chicago (ORD)

Frontier Airlines • Non-stop • Coach

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Non-stop • Coach
Price was $683, price is now $460 per person
$460
per person
found 1 day ago
Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

Apr 19 - Apr 23

4 night stay

Boston (BOS) to Chicago (ORD)

American Airlines • Coach

Chicago (ORD) to Boston (BOS)

JetBlue Airways • Coach
Save 100% on your flight
Price was $975, price is now $673 per person
$673
per person
found 18 hours ago
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Oak Brook premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Sentral Michigan Avenue
4.0-star property

Sentral Michigan Avenue

9.2/10 Wonderful! (983 reviews)

Mar 27 - Mar 29

2 night stay

New York (NYC) to Chicago (ORD)

Delta • PremiumEconomy

Chicago (ORD) to New York (NYC)

JetBlue Airways • PremiumEconomy
Price was $636, price is now $580 per person
$580
per person
found 20 hours ago
Everything was perfect I will be back in Chicago and will use you guys all the time. Thank you for making my stay amazing and so cozy.

Reviewed on Nov 22, 2025

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (2,790 reviews)

Apr 6 - Apr 8

2 night stay

Los Angeles (LAX) to Chicago (ORD)

United • PremiumEconomy

Chicago (ORD) to Los Angeles (LAX)

Delta • PremiumEconomy
Price was $959, price is now $826 per person
$826
per person
found 1 day ago
I recommend 100% Everything was good, the staff, room and the food. Also, it is located in a good area.

Reviewed on Jan 14, 2026

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,773 reviews)

Apr 6 - Apr 8

2 night stay

Los Angeles (LAX) to Chicago (ORD)

United • PremiumEconomy

Chicago (ORD) to Los Angeles (LAX)

Delta • PremiumEconomy
Price was $1,244, price is now $1,119 per person
$1,119
per person
found 1 day ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!

Reviewed on Oct 13, 2025

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Oak Brook 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! (2,790 reviews)

Mar 29 - Apr 1

3 night stay

Los Angeles (LAX) to Chicago (ORD)

American Airlines • FirstClass

Chicago (ORD) to Los Angeles (LAX)

Spirit Airlines • FirstClass
Price was $1,062, price is now $861 per person
$861
per person
found 11 hours ago
I recommend 100% Everything was good, the staff, room and the food. Also, it is located in a good area.

Reviewed on Jan 14, 2026

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,773 reviews)

Mar 29 - Apr 1

3 night stay

Los Angeles (LAX) to Chicago (ORD)

American Airlines • FirstClass

Chicago (ORD) to Los Angeles (LAX)

Spirit Airlines • FirstClass
Price was $1,539, price is now $1,212 per person
$1,212
per person
found 11 hours ago
Food was amazing and the staff was amazing. Room was incredible! Felt like we were royalty on our visit!

Reviewed on Oct 13, 2025

Waldorf Astoria Chicago
5.0-star property

Waldorf Astoria Chicago

9.4/10 Exceptional! (1,000 reviews)

Mar 29 - Apr 1

3 night stay

Los Angeles (LAX) to Chicago (ORD)

American Airlines • FirstClass

Chicago (ORD) to Los Angeles (LAX)

Spirit Airlines • FirstClass
Price was $1,738, price is now $1,494 per person
$1,494
per person
found 11 hours ago
Lovely room and spacious bathroom plus all of the high end touches (robes, slippers to soft mats and towels and great bath products and loved the nespresso maker!) View was not great but gym and lobby made up for it; bar was too crowded and we couldn’t get a late checkout but at least it was noon and they held our bags for a few hours!

Reviewed on Dec 31, 2025

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Oak Brook

Orbitz uses cutting edge mobile technology to help get you the best deals on Oak Brook flights. We offer guaranteed low prices on air tickets that can be combined with hotels and car rentals to save you even more money.

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Use the Orbitz Flight Matrix To Save Big On Car Rental

Discount flights to Oak Brook can be combined with car rental to get you additional savings. Just use our Flight Matrix to see how your budget air ticket can be combined with a car rental to make your trip not only inexpensive but also more convenient.

Use Multiple Airlines To Ensure You Get The Best Deal

Orbitz allows you to use multiple airlines for flights to Oak Brook. By using a combination of airlines for discount flights you are guaranteed to get the lowest fares each way and get the schedule that is most convenient for you.

Store Your Frequent Flyer Information on Orbitz For Easy Access

Booking with Orbitz will still allow you to apply miles for flights to Oak Brook to your frequent flyer program. Not only that, but your frequent flyer information will be safely stored on our website, so it will be easy to access the next time you book a discount air ticket with Orbitz.

Frequently asked questions

Which airlines fly to Oak Brook?
Take your pick of 20 airlines that operate services to O'Hare Intl. Airport (ORD), the most popular airport in the city. With a good range of options, you're sure to find an awesome deal. Here are some of the top international carriers that'll get you to Oak Brook:

  • United Airlines - 612 flights to Oak Brook per month
  • American Airlines - 339 flights to Oak Brook per month
  • Air Canada - 190 flights to Oak Brook per month

What is the best airport to fly to in Oak Brook?
Reserve a flight to O'Hare Intl. Airport (ORD) and get set to discover every corner of this terrific city. The airport is around 10 miles north of the center of town. Also check out the price of flights to Midway Intl. Airport (MDW), which is another entrance point to Oak Brook.
How much is a flight to Oak Brook?
Prices for return flights dipped as low as $56 this past week to Oak Brook, and reached a high of $147. Several lucky travelers departing New York (EWR) managed to secure one-way fares from just $28.
How to book the cheapest flight to Oak Brook?
With some of the biggest and best flight deals around, you'll get more for your money with Orbitz. The following tips and hints will help you find cheap flights to Oak Brook — and leave you with more money in your pocket:

  • Consider other airports to save on your airfare. Enter your preferred departure and arrival airports in the form fields, then choose the 'Nearby airports' function below. It will list the available options.
  • If you're flexible with your travel plans, click on the 'Show flexible dates' link. It'll display the flight deals for the days around your chosen departure. Fares often vary depending on the day of the week.
  • Select 'Show options' to refine 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.
  • Book your airfare as soon as you've decided on your travel dates. While it does happen on occasion, tickets rarely get more affordable as your date of departure gets closer.
  • Save on your trip by bundling your flights, hotels and car rentals into a package deal. Your bank account will thank you.
  • Flying during busier seasons often means steep airfares. Try to plan your trip outside of popular dates, such as Easter, Thanksgiving and school breaks.

How long is a flight to Oak Brook?
The USA is big, so that depends on the destination you're departing from. To make things simple, we've chosen three of the most well-known routes to Oak Brook and worked out 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 Oak Brook?
Catch a bargain and secure your seats to Oak Brook in January. If you've missed this month, fear not. February and August often have low airfares available, too. Be careful not to sleep on a sale — cheap flights emerge and disappear in the blink of an eye!
What day of the week is the cheapest to book a flight to Oak Brook?
When it comes to cheap airfares to Oak Brook, the best days to book are generally Tuesdays, Wednesdays and Saturdays. A fantastic flight deal is just a few clicks away with Orbitz.
What is the cheapest day of the week to fly to Oak Brook?
Consider departing early in the week to score cheap flights to Oak Brook. Orbitz data from 2020 indicates Monday is normally the most inexpensive day to start your trip, followed by Tuesday. Saturday was found to have the highest ticket prices. This is possibly because many travelers choose to start their vacation after a long working week.
What is the cheapest month to fly to Oak Brook?
You can jet for less in August. This is generally the best month to get on a plane if you're after cheap flights to Oak Brook, Orbitz data shows. The most expensive time to fly is June, so avoid this month if you can.
Which airlines allow free cancellation?
We understand that plans change and flexibility is important. That's why you can search for flights that have free cancellation and no change fees on Orbitz. Simply click on "Filter by flexible change policies" and we'll show you fares with more flexibility than a crayon left in the sun!
What do I need for the flight to Oak Brook?
Nothing beats jetting someplace new, but it's wise to be prepared. This list of top tips will help get your journey started on the right foot:

  • Your travel documents are the most important things you'll need to take with you on your flight. To avoid any dramas during check-in, make sure that the information displayed on your ticket matches your government-issued ID.
  • Make time fly by even faster on your short hop by packing the right things. Think yummy snacks, bottled water and entertainment. If you'd like your journey to Oak Brook to go nice and peacefully, put some headphones into your bag as well.
  • It can get very cool on the plane. If you don't like the idea of shivering your way through the flight, layer up.

How many direct flights are there to Oak Brook?
You can catch one of 2,332 flights that travel directly to Oak Brook every month. United Airlines, American Airlines and Delta Air Lines are just a few of the carriers that will get you there comfortably in one go. Southwest Airlines, Spirit Airlines and Air Canada are some other carriers that fly to Oak Brook nonstop.
How do I get cheap first-class/business deals to Oak Brook?
If you think a business or first-class airfare is way out of your reach, you may want to think again. Here are some practical tips to help you land a premium flight to Oak Brook for a whole lot less:

  • Be flexible with your travel dates and wait for big sales on business or first-class airfares.
  • Search for a budget carrier that offers business-class seats. They often come with more legroom and a glass of bubbly — but without the high price.
  • Make the most of your airline's frequent flyer program and use points to upgrade your seat. Alternatively, you can try bidding for an upgrade in an online auction if available.

How to get into Oak Brook from the airport?
Head for downtown Oak Brook with an O'Hare Intl. Airport (ORD) car rental. There are two suppliers at O'Hare Intl. Airport (ORD) — Thrifty Car Rental and Dollar. After you've signed some papers and collected the keys to your ride, the city center is a journey of 10 miles to the south of ORD. You could also take a taxi into town and drive away in a vehicle from one of our Oak Brook car rentals. Whatever you decide, when you book with Orbitz, you can be sure you'll always bag a fabulous deal!
What is the best time to go to Oak Brook?
You'll have all the fun you can handle no matter what time of year you choose to go to Oak Brook, but May, June and July are the most popular months. Like to pack your itinerary with stacks of warm-weather activities? Book your getaway around June 20. This is when the summer season kicks off in the Northern Hemisphere. Expect the mercury to sit anywhere between 65 ºF and 80 ºF at this time.
Travel tips for Oak Brook

  • Kick off your sightseeing in the downtown area and take a self-guided walking tour of the city's awesome attractions. Oakbrook Center Mall and Yorktown Shopping Center are a couple of visitor favorites.
  • You'll discover fun day trip adventures a short drive from Oak Brook's center. Take in Wrigley Field first and then McCormick Place.
  • Get your bum in the driver's seat and discover what else makes Chicago a tourism hot spot. Arrange a car rental with Orbitz and enjoy the delights of two more must-do cities — Gurnee and Waukegan.

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.