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.

Sat, May 9 - Tue, May 12
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$56 Roundtrip, found 19 hours ago
$56
Roundtrip
found 19 hours ago
Select Frontier Airlines flight, departing Sat, May 9 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, May 12, priced at $56 found 19 hours ago
Wed, Apr 29 - Sat, May 2
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$56 Roundtrip, found 7 hours ago
$56
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Wed, Apr 29 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Sat, May 2, priced at $56 found 7 hours ago
Thu, Apr 16 - Sun, Apr 19
PHX
Sky Harbor Intl.
MDW
Midway Intl.
$68 Roundtrip, found 6 days ago
$68
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Thu, Apr 16 from Sky Harbor Intl. to Midway Intl., returning Sun, Apr 19, priced at $68 found 6 days ago
Sat, Apr 18 - Sat, May 2
PHX
Sky Harbor Intl.
ORD
O'Hare Intl.
$72 Roundtrip, found 4 days ago
$72
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Apr 18 from Sky Harbor Intl. to O'Hare Intl., returning Sat, May 2, priced at $72 found 4 days ago
Sat, May 2 - Mon, May 4
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$76 Roundtrip, found 5 days ago
$76
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, May 2 from Los Angeles Intl. to O'Hare Intl., returning Mon, May 4, priced at $76 found 5 days ago
Sat, May 9 - Wed, May 13
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$76 Roundtrip, found 3 hours ago
$76
Roundtrip
found 3 hours ago
Select Spirit Airlines flight, departing Sat, May 9 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Wed, May 13, priced at $76 found 3 hours ago
Wed, Apr 29 - Sat, May 2
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$106 Roundtrip, found 4 days ago
$106
Roundtrip
found 4 days ago
Select American Airlines flight, departing Wed, Apr 29 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Sat, May 2, priced at $106 found 4 days ago
Fri, May 1 - Mon, May 4
MSP
Minneapolis - St. Paul Intl.
MDW
Midway Intl.
$116 Roundtrip, found 6 days ago
$116
Roundtrip
found 6 days ago
Select Delta flight, departing Fri, May 1 from Minneapolis - St. Paul Intl. to Midway Intl., returning Mon, May 4, priced at $116 found 6 days ago
Mon, Apr 27 - Mon, May 4
MSP
Minneapolis - St. Paul Intl.
ORD
O'Hare Intl.
$129 Roundtrip, found 4 days ago
$129
Roundtrip
found 4 days ago
Select United flight, departing Mon, Apr 27 from Minneapolis - St. Paul Intl. to O'Hare Intl., returning Mon, May 4, priced at $129 found 4 days ago
Sat, May 9 - Tue, May 12
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$138 Roundtrip, found 19 hours ago
$138
Roundtrip
found 19 hours ago
Select American Airlines flight, departing Sat, May 9 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Tue, May 12, priced at $138 found 19 hours ago

Oak Brook Flight Information

Traveling To
Oak Brook
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, United, Delta, Southwest Airlines, 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.
Illinois Beach Hotel
2.0-star property

Illinois Beach Hotel

Apr 8 - Apr 11

3 night stay

Dallas (DFW) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $261, price is now $191 per person
$191
per person
found 1 day ago
La Banque Hotel
4.0-star property

La Banque Hotel

Apr 15 - Apr 18

3 night stay

Dallas (DFW) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $549, price is now $373 per person
$373
per person
found 1 day ago
Pendry Chicago
4.5-star property

Pendry Chicago

Apr 8 - Apr 11

3 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $650, price is now $452 per person
$452
per person
found 1 day ago
Don't see what you're looking for?
See all available trips from Dallas to Oak Brook
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Oak Brook premium economy flight packages

Price found within the past 48 hours. Click for updated prices.
Illinois Beach Hotel
2.0-star property

Illinois Beach Hotel

8/10 Very Good! (503 reviews)

Apr 15 - Apr 19

4 night stay

San Juan (SJU) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $758, price is now $683 per person
$683
per person
found 16 hours ago
Private beach on Lake Michigan. Very beautiful.Nature trails right out side the door. Great staff . Good restaurant.

Reviewed on Oct 20, 2024

Baymont by Wyndham Gurnee
2.5-star property

Baymont by Wyndham Gurnee

7.8/10 Good! (1,004 reviews)

Apr 15 - Apr 19

4 night stay

San Juan (SJU) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $786, price is now $708 per person
$708
per person
found 16 hours ago
It's quiet and clean and close to the facilities we visit in the area. It's a favorite. Not much we can say negative about it.

Reviewed on Jul 15, 2025

Holiday Inn Express & Suites Zion by IHG
2.5-star property

Holiday Inn Express & Suites Zion by IHG

8.8/10 Excellent! (183 reviews)

Apr 15 - Apr 19

4 night stay

San Juan (SJU) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $861, price is now $777 per person
$777
per person
found 16 hours ago
Don't see what you're looking for?
See all available trips from San Juan to Oak Brook
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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)

Apr 21 - Apr 24

3 night stay

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

American Airlines • FirstClass

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

Spirit Airlines • FirstClass
Price was $971, price is now $722 per person
$722
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

LondonHouse Chicago, Curio Collection by Hilton
4.5-star property

LondonHouse Chicago, Curio Collection by Hilton

9.4/10 Exceptional! (3,595 reviews)

Apr 21 - Apr 24

3 night stay

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

American Airlines • FirstClass

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

Spirit Airlines • FirstClass
Price was $1,268, price is now $1,018 per person
$1,018
per person
found 1 day ago
Everything from the staff to the hotel was AWESOME‼️‼️

Reviewed on Feb 15, 2026

Fairmont Chicago at Millennium Park
4.5-star property

Fairmont Chicago at Millennium Park

8.6/10 Excellent! (2,008 reviews)

Apr 21 - Apr 24

3 night stay

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

American Airlines • FirstClass

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

Spirit Airlines • FirstClass
Price was $960, price is now $776 per person
$776
per person
found 1 day ago
The room was great the service was good

Reviewed on Feb 16, 2026

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Oak Brook

Get the absolute lowest prices on flights to Oak Brook 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 Oak Brook

Orbitz also provides an array of resources that can help you eliminate most check-in hassles. Detailed baggage information is continually available for Oak Brook 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 Oak Brook flight using 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 $138. Several lucky travelers departing Atlanta (ATL) 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.