Cheap flights To Oak Brook (CHI) from $59

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Cheap Flights to Oak Brook from $59 One Way, $108 Round Trip

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

Sat, Nov 7 - Sat, Nov 14
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$108 Roundtrip, found 6 days ago
$108
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Sat, Nov 7 from Dallas-Fort Worth Intl. to Midway Intl., returning Sat, Nov 14, priced at $108 found 6 days ago
Sat, Oct 24 - Mon, Oct 26
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$118 Roundtrip, just found
$118
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Oct 24 from Los Angeles Intl. to O'Hare Intl., returning Mon, Oct 26, priced at $118 just found
Wed, Oct 14 - Mon, Oct 19
MCO
Orlando Intl.
ORD
O'Hare Intl.
$136 Roundtrip, found 1 hour ago
$136
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, Oct 14 from Orlando Intl. to O'Hare Intl., returning Mon, Oct 19, priced at $136 found 1 hour ago
Thu, Dec 3 - Thu, Dec 3
MCO
Orlando Intl.
MDW
Midway Intl.
$177 Roundtrip, found 6 days ago
$177
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Dec 3 from Orlando Intl. to Midway Intl., returning Thu, Dec 3, priced at $177 found 6 days ago
Thu, Oct 22 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 4 hours ago
$197
Roundtrip
found 4 hours ago
Select American Airlines flight, departing Thu, Oct 22 from Los Angeles Intl. to O'Hare Intl., returning Sat, Oct 24, priced at $197 found 4 hours ago
Fri, Oct 16 - Mon, Oct 19
LAX
Los Angeles Intl.
MDW
Midway Intl.
$197 Roundtrip, found 12 hours ago
$197
Roundtrip
found 12 hours ago
Select Southwest Airlines flight, departing Fri, Oct 16 from Los Angeles Intl. to Midway Intl., returning Mon, Oct 19, priced at $197 found 12 hours ago
Thu, Nov 5 - Fri, Nov 6
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 1 hour ago
$197
Roundtrip
found 1 hour ago
Select United flight, departing Thu, Nov 5 from Los Angeles Intl. to O'Hare Intl., returning Fri, Nov 6, priced at $197 found 1 hour ago
Thu, Oct 22 - Sat, Oct 24
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$197 Roundtrip, found 4 hours ago
$197
Roundtrip
found 4 hours ago
Select Delta flight, departing Thu, Oct 22 from Los Angeles Intl. to O'Hare Intl., returning Sat, Oct 24, priced at $197 found 4 hours ago
Thu, Nov 12 - Sat, Nov 14
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$203 Roundtrip, found 13 hours ago
$203
Roundtrip
found 13 hours ago
Select Frontier Airlines flight, departing Thu, Nov 12 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Nov 14, priced at $203 found 13 hours ago
Tue, Sep 22 - Sat, Sep 26
LAX
Los Angeles Intl.
RFD
Greater Rockford
$217 Roundtrip, found 1 day ago
$217
Roundtrip
found 1 day ago
Select American Airlines flight, departing Tue, Sep 22 from Los Angeles Intl. to Greater Rockford, returning Sat, Sep 26, priced at $217 found 1 day ago

Oak Brook Flight Information

Traveling To
Oak Brook
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Frontier Airlines, American Airlines, Southwest Airlines, Delta, United
Flight Price
$108
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 Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

Oct 19 - Oct 23

4 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Coach

Chicago (ORD) to Boston (BOS)

Frontier Airlines • Coach
Price was $1,097, price is now $721 per person
$721
per person
found 1 day ago
Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

Oct 19 - Oct 23

4 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Coach

Chicago (ORD) to Boston (BOS)

Frontier Airlines • Coach
Price was $1,925, price is now $1,098 per person
$1,098
per person
found 1 day ago
Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

Oct 19 - Oct 23

4 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Coach

Chicago (ORD) to Boston (BOS)

Frontier Airlines • Coach
Price was $1,690, price is now $985 per person
$985
per person
found 1 day ago
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Oak Brook premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

8.2/10 Very Good! (2,899 reviews)

Oct 2 - Oct 6

4 night stay

New York (NYC) to Chicago (ORD)

JetBlue Airways • PremiumEconomy

Chicago (ORD) to New York (NYC)

Frontier Airlines • PremiumEconomy
Price was $1,063, price is now $827 per person
$827
per person
found 1 day ago

Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

9.2/10 Wonderful! (550 reviews)

Oct 2 - Oct 6

4 night stay

New York (NYC) to Chicago (ORD)

JetBlue Airways • PremiumEconomy

Chicago (ORD) to New York (NYC)

Frontier Airlines • PremiumEconomy
Save 100% on your flight
Price was $1,458, price is now $1,066 per person
$1,066
per person
found 1 day ago
Will stay here everytime in Chicago . Perfect location, units clean and well put together . Great amsninities.

Reviewed on Aug 24, 2026

Hilton Garden Inn Chicago Downtown South Loop
3.0-star property

Hilton Garden Inn Chicago Downtown South Loop

8.8/10 Excellent! (2,116 reviews)

Oct 2 - Oct 6

4 night stay

New York (NYC) to Chicago (ORD)

JetBlue Airways • PremiumEconomy

Chicago (ORD) to New York (NYC)

Frontier Airlines • PremiumEconomy
Price was $1,558, price is now $1,213 per person
$1,213
per person
found 1 day ago
Phone didnt work. Couldn't call for help or extra amenities. Valet who said they were 24/7 were not and left me with my car for the whole night I was out and about. Staff was no help even after bring these things to their attention. I would not opt in staying here again.

Reviewed on Aug 24, 2026

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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! (4,907 reviews)

Sep 27 - Sep 29

2 night stay

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

American Airlines • Roundtrip • FirstClass
Price was $1,121, price is now $891 per person
$891
per person
just found
Beautiful new LEED hotel. Staff were exceptional. Unique part of the room was that you had to place your room key in reader inside your room in order to activate electricity ( room Lights,TV, etc.). I suggest they make visitors aware when they check in. Liked the safety features with the elevator too.

Reviewed on Aug 24, 2026

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.6/10 Exceptional! (1,960 reviews)

Sep 26 - Sep 28

2 night stay

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

American Airlines • Roundtrip • FirstClass
Price was $1,351, price is now $1,119 per person
$1,119
per person
found 1 day ago

Level Chicago - River North
4.0-star property

Level Chicago - River North

9.2/10 Wonderful! (1,055 reviews)

Sep 26 - Sep 29

3 night stay

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

American Airlines • Roundtrip • FirstClass
Price was $1,231, price is now $1,030 per person
$1,030
per person
found 1 day ago
Front desk staff where very unprofessional - friends of theirs hanging out at the desk and when asked for assistance it was as if we were bothering them. housekeeping staff was excellent and attentive when we had to ask for extra bedding and towels since we were 4 not 2pp - these extra items should have been in the room at check in. Pool deck, hot tub, exercise room and sauna/steam area are all top notch. We really loved the concept but would have liked more of a customer service oriented stay.

Reviewed on Aug 23, 2026

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Oak Brook

If you are looking for affordable flights to Oak Brook, look no further. Orbitz offers discounted rates to many destinations.

Bargain flights to Oak Brook now available

As you review your budget and travel plans, consider the low fares Orbitz offers on Oak Brook flights. With Orbitz, booking flights to Oak Brook is easy and the lowest prices are guaranteed.

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Orbitz offers cutting edge mobile tools that allow you to review and make bookings from your Android or iPhone mobile device with a simple application. You can easily and conveniently update your information or book your trip using this service. You are also able to obtain information on affordable hotel packages and receive frequent flight updates. You will receive confirmation of bookings or reservations made using the mobile service on the same day of the request. Change details or receive updates on your Oak Brook flights by visiting the Orbitz site or mobile application.

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Orbitz ensures that you are kept informed with up-to-date flight information, providing feedback to up to six contact numbers to ensure that everyone receives the feedback. In addition to providing the discounted deals on Oak Brook flights, Orbitz is also able to structure a package based on your needs for activities, car hire and accommodations.

Traveler profile updates

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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 $108 this past week to Oak Brook, and reached a high of $217. Several lucky travelers departing Los Angeles (LAX) managed to secure one-way fares from just $59.
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.