Cheap flights To Oak Brook (CHI) from $29

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Cheap Flights to Oak Brook from $29 One Way, $53 Round Trip

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

Sat, Jan 24 - Sat, Jan 24
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$53 Roundtrip, found 2 days ago
$53
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sat, Jan 24 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Sat, Jan 24, priced at $53 found 2 days ago
Tue, Dec 16 - Tue, Dec 16
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$54 Roundtrip, found 3 days ago
$54
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Dec 16 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Dec 16, priced at $54 found 3 days ago
Thu, Feb 26 - Sat, Feb 28
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$64 Roundtrip, found 2 days ago
$64
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Thu, Feb 26 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Feb 28, priced at $64 found 2 days ago
Tue, Jan 13 - Thu, Jan 15
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$66 Roundtrip, just found
$66
Roundtrip
just found
Select Frontier Airlines flight, departing Tue, Jan 13 from Newark Liberty Intl. Airport to Midway Intl., returning Thu, Jan 15, priced at $66 just found
Wed, Jan 7 - Sat, Jan 10
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$67 Roundtrip, found 2 days ago
$67
Roundtrip
found 2 days ago
Select Spirit Airlines flight, departing Wed, Jan 7 from Newark Liberty Intl. Airport to O'Hare Intl., returning Sat, Jan 10, priced at $67 found 2 days ago
Thu, Feb 26 - Mon, Mar 2
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$68 Roundtrip, just found
$68
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Feb 26 from John F. Kennedy Intl. to O'Hare Intl., returning Mon, Mar 2, priced at $68 just found
Fri, Feb 20 - Mon, Feb 23
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$68 Roundtrip, found 20 hours ago
$68
Roundtrip
found 20 hours ago
Select Frontier Airlines flight, departing Fri, Feb 20 from Dallas-Fort Worth Intl. to Midway Intl., returning Mon, Feb 23, priced at $68 found 20 hours ago
Sat, Jan 17 - Tue, Jan 20
DAL
Love Field
MDW
Midway Intl.
$84 Roundtrip, found 3 days ago
$84
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Jan 17 from Love Field to Midway Intl., returning Tue, Jan 20, priced at $84 found 3 days ago
Sat, Jan 17 - Tue, Jan 20
DAL
Love Field
ORD
O'Hare Intl.
$84 Roundtrip, found 3 days ago
$84
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Sat, Jan 17 from Love Field to O'Hare Intl., returning Tue, Jan 20, priced at $84 found 3 days ago
Wed, Feb 4 - Tue, Feb 10
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$91 Roundtrip, found 1 day ago
$91
Roundtrip
found 1 day ago
Select United flight, departing Wed, Feb 4 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Tue, Feb 10, priced at $91 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, United, Southwest Airlines
Flight Price
$53
Earliest Departing Flight
Latest Departing Flight

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

Jan 8 - Jan 10

2 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $302, price is now $208 per person
$208
per person
found 1 day ago
Arlo Chicago
4.0-star property

Arlo Chicago

Jan 15 - Jan 19

4 night stay

Boston (BOS) to Chicago (ORD)

Delta • Coach

Chicago (ORD) to Boston (BOS)

United • Coach
Save 100% on your flight
Price was $541, price is now $353 per person
$353
per person
found 1 day ago
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Jan 15 - Jan 19

4 night stay

Boston (BOS) to Chicago (ORD)

Delta • Coach

Chicago (ORD) to Boston (BOS)

United • Coach
Save 100% on your flight
Price was $1,095, price is now $743 per person
$743
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Boston to Oak Brook
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Oak Brook premium 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

9.4/10 Exceptional! (2,790 reviews)

Jan 16 - Jan 19

3 night stay

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

Delta • Non-stop • PremiumEconomy

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

United • Non-stop • PremiumEconomy
Price was $703, price is now $545 per person
$545
per person
found 1 day ago
One day didn’t receive room service

Reviewed on Sep 2, 2025

Eurostars Magnificent Mile
4.0-star property

Eurostars Magnificent Mile

8.8/10 Excellent! (3,098 reviews)

Jan 16 - Jan 19

3 night stay

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

Delta • Non-stop • PremiumEconomy

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

United • Non-stop • PremiumEconomy
Price was $841, price is now $655 per person
$655
per person
found 1 day ago
In convenient area either by walking or uber

Reviewed on Oct 18, 2025

Hotel Chicago Downtown, Autograph Collection by Marriott
4.0-star property

Hotel Chicago Downtown, Autograph Collection by Marriott

9/10 Wonderful! (1,003 reviews)

Jan 16 - Jan 19

3 night stay

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

Delta • Non-stop • PremiumEconomy

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

United • Non-stop • PremiumEconomy
Price was $712, price is now $559 per person
$559
per person
found 1 day ago
Had a wonderful two nights stay. The staff were all extremely friendly and the room was very comfortable.

Reviewed on Jun 11, 2025

Don't see what you're looking for?
See all available trips from Newark Liberty Intl. Airport to Oak Brook
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Oak Brook

Orbitz is your one stop for guaranteed low prices on Oak Brook flights, as well as budget deals on hotels and rental cars. Use our state of the art mobile tools to get great deals and constant updates on the status of your trip.

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Orbitz will find you discount air fare for flights to Oak Brook and you can rent a car at the same time. With Orbitzyou will get a discount on the rental and have your car waiting for you when you land.

Get Free Travel Advice By Calling the Orbitz Hotline

Our experts will make things even easier by helping you to find the best budget flights to Oak Brook Just call our toll free hotline at 1-800-649-9920 and one of our travel advisors will be happy to assist you with everything from your flight to hotel room.

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Our state of the art mobile apps will allow you to book cheap flights to Oak Brook from your smartphone too. Discount airfare is not all; you can also find mobile-only hotel deals or check the status of your flight using this free app. So, when you’re on the go, why not take Orbitz with you?

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 $53 this past week to Oak Brook, and reached a high of $91. Several lucky travelers departing Atlanta (ATL) managed to secure one-way fares from just $29.
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.