Cheap flights To Oak Brook (CHI)

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Oak Brook Flight Information

Traveling To
Oak Brook
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Flight Price
Earliest Departing Flight
Latest Departing Flight

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Oak Brook economy flight packages

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
4.0-star property

Level Chicago – Old Town

Jul 15 - Jul 18

3 night stay

Boston (BOS) to Chicago (ORD)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,069, price is now $705 per person
$705
per person
found 19 hours ago
Level Chicago Fulton Market
4.0-star property

Level Chicago Fulton Market

Jul 27 - Jul 31

4 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,343, price is now $854 per person
$854
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

Jul 27 - Jul 31

4 night stay

Boston (BOS) to Chicago (ORD)

JetBlue Airways • Roundtrip • Coach
Save 100% on your flight
Price was $1,171, price is now $782 per person
$782
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.
Swissotel - Chicago
4.5-star property

Swissotel - Chicago

9/10 Wonderful! (3,352 reviews)

Jul 6 - Jul 13

7 night stay

New York (NYC) to Chicago (ORD)

JetBlue Airways • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,451, price is now $965 per person
$965
per person
found 21 hours ago
Great stay and we highly recommend. We will be back.

Reviewed on Apr 21, 2026

Hotel Riu Plaza Chicago
4.0-star property

Hotel Riu Plaza Chicago

9.4/10 Exceptional! (4,258 reviews)

Jul 6 - Jul 13

7 night stay

New York (NYC) to Chicago (ORD)

JetBlue Airways • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $2,045, price is now $1,337 per person
$1,337
per person
found 21 hours ago
Great option! Great location! Great breakfast and friendly staff!

Reviewed on May 30, 2026

Hotel Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

8.2/10 Very Good! (2,732 reviews)

Jul 6 - Jul 13

7 night stay

New York (NYC) to Chicago (ORD)

JetBlue Airways • Roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,485, price is now $1,022 per person
$1,022
per person
found 21 hours ago
Best vibe. In the mix!

Reviewed on May 2, 2026

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Oak Brook first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hilton Chicago O'Hare Airport
4.0-star property

Hilton Chicago O'Hare Airport

8.4/10 Very Good! (2,310 reviews)

Jul 25 - Jul 27

2 night stay

Philadelphia (PHL) to Chicago (ORD)

United • Roundtrip • FirstClass
Price was $930, price is now $823 per person
$823
per person
found 1 day ago
This place gets 3 stars from me only due to its great location. It's in rather poor repair and its overall appearance and upkeep do not reflect well on the Hilton brand. It seems clear that property ownership are not bothering to put money into it because they know they will get traffic from the airport.

Reviewed on Feb 25, 2026

Hotel Felix River North/Magnificent Mile
4.0-star property

Hotel Felix River North/Magnificent Mile

8.2/10 Very Good! (2,732 reviews)

Jul 25 - Jul 27

2 night stay

Philadelphia (PHL) to Chicago (ORD)

United • Roundtrip • FirstClass
Price was $1,004, price is now $861 per person
$861
per person
found 1 day ago
Best vibe. In the mix!

Reviewed on May 2, 2026

Kimpton Gray Hotel by IHG
4.5-star property

Kimpton Gray Hotel by IHG

9.4/10 Exceptional! (1,005 reviews)

Jul 25 - Jul 27

2 night stay

Philadelphia (PHL) to Chicago (ORD)

United • Roundtrip • FirstClass
Price was $1,100, price is now $947 per person
$947
per person
found 1 day ago
I absolutely loved my stay at this property! Everything—from the warm, welcoming atmosphere to the beautifully maintained rooms—made the experience unforgettable. The staff were incredibly kind, and every detail felt thoughtfully designed for comfort. I can’t wait to come back!

Reviewed on Nov 21, 2025

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Oak Brook

Why search for low cost fares on your flights to Oak Brook when Orbitz offers the guaranteed lowest prices on foreign and domestic flights? When you travel with Orbitz you can benefit from:

Bargain Flights to Oak Brook

Orbitz offers massive discounts and substantial last-minute savings on your Oak Brook flights. Orbitz ensures that you can find, plan and reserve your flights any destination with ease, all while enjoying the guaranteed lowest prices available anywhere.

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Orbitz sends you free alerts and updates on your Oak Brook flight wherever you are in the world. Once you have downloaded the free app for your iPhone, Android, or iPad, you can review or alter any travel plans that you have made or even book a future flight for business or pleasure. If you need to reserve a hotel room when booking your flight, you will find exclusive deals on our mobile site.

Frequent Flyer Program Enrolment

Orbitz finds you the lowest fares, but you can still add your miles to your frequent flyer program to earn miles or points on selected flights to Oak Brook. When making your booking, reference your frequent flyer number to receive discounts in the future.

Outstanding Customer Service

Orbitz values your business and wants to ensure that all of your flights are as easy as possible to book. If you have booked a flight to Oak Brook but need to cancel it, you may be able to do so online. If you have any questions or need help, the dedicated Orbitz customer service team is always standing by.

Frequently asked questions

Which airlines fly to Oak Brook?
Take your pick of 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 this past week to Oak Brook, and reached a high of . Several lucky travelers departing () managed to secure one-way fares from just .
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.