Cheap flights To Oakbrook Terrace (CHI) from $25

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Cheap Flights to Oakbrook Terrace from $25 One Way, $49 Round Trip

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

Tue, Oct 14 - Tue, Oct 21
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$49 Roundtrip, found 3 days ago
$49
Roundtrip
found 3 days ago
Select Frontier Airlines flight, departing Tue, Oct 14 from Newark Liberty Intl. Airport to Midway Intl., returning Tue, Oct 21, priced at $49 found 3 days ago
Sat, Nov 15 - Wed, Nov 19
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$74 Roundtrip, found 5 days ago
$74
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Nov 15 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Wed, Nov 19, priced at $74 found 5 days ago
Wed, Oct 29 - Sat, Nov 1
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$75 Roundtrip, found 5 days ago
$75
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Wed, Oct 29 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Sat, Nov 1, priced at $75 found 5 days ago
Tue, Oct 7 - Wed, Oct 8
LGA
LaGuardia
ORD
O'Hare Intl.
$77 Roundtrip, found 4 hours ago
$77
Roundtrip
found 4 hours ago
Select Spirit Airlines flight, departing Tue, Oct 7 from LaGuardia to O'Hare Intl., returning Wed, Oct 8, priced at $77 found 4 hours ago
Wed, Dec 10 - Tue, Dec 16
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$77 Roundtrip, found 6 days ago
$77
Roundtrip
found 6 days ago
Select Frontier Airlines flight, departing Wed, Dec 10 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Dec 16, priced at $77 found 6 days ago
Wed, Feb 11 - Wed, Feb 18
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$91 Roundtrip, found 11 hours ago
$91
Roundtrip
found 11 hours ago
Select Spirit Airlines flight, departing Wed, Feb 11 from Newark Liberty Intl. Airport to O'Hare Intl., returning Wed, Feb 18, priced at $91 found 11 hours ago
Tue, Oct 7 - Tue, Oct 7
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$94 Roundtrip, found 16 hours ago
$94
Roundtrip
found 16 hours ago
Select Frontier Airlines flight, departing Tue, Oct 7 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Oct 7, priced at $94 found 16 hours ago
Thu, Dec 4 - Thu, Dec 11
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$100 Roundtrip, found 9 hours ago
$100
Roundtrip
found 9 hours ago
Select Spirit Airlines flight, departing Thu, Dec 4 from Baltimore Washington Intl. Thurgood Marshall to O'Hare Intl., returning Thu, Dec 11, priced at $100 found 9 hours ago
Sat, Oct 18 - Mon, Oct 20
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$105 Roundtrip, found 5 days ago
$105
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Oct 18 from Baltimore Washington Intl. Thurgood Marshall to Midway Intl., returning Mon, Oct 20, priced at $105 found 5 days ago
Sat, Dec 6 - Tue, Dec 9
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$137 Roundtrip, found 16 hours ago
$137
Roundtrip
found 16 hours ago
Select Southwest Airlines flight, departing Sat, Dec 6 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Tue, Dec 9, priced at $137 found 16 hours ago

Oakbrook Terrace Flight Information

Traveling To
Oakbrook Terrace
Destination Airport IATA Code
CHI
Number of Airlines Serving
Airlines
Frontier Airlines, Spirit Airlines, Southwest Airlines
Flight Price
$49
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

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Oakbrook Terrace economy flight packages

Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago
5.0-star property

Park Hyatt Chicago

Oct 24 - Oct 26

2 night stay

Dallas (DFW) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,000, price is now $721 per person
$721
per person
found 17 hours ago
Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

Oct 25 - Oct 28

3 night stay

Dallas (DFW) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,235, price is now $825 per person
$825
per person
found 1 day ago
Pendry Chicago
4.5-star property

Pendry Chicago

Oct 31 - Nov 4

4 night stay

Dallas (DFW) to Chicago (ORD)

Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,130, price is now $822 per person
$822
per person
found 1 day ago
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Oakbrook Terrace 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! (2,427 reviews)

Nov 7 - Nov 11

4 night stay

Los Angeles (LAX) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Price was $1,094, price is now $777 per person
$777
per person
found 1 hour ago
One day didn’t receive room service

Reviewed on Sep 2, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile
3.5-star property

Hilton Grand Vacations Club Chicago Magnificent Mile

9.2/10 Wonderful! (289 reviews)

Oct 22 - Oct 26

4 night stay

Phoenix (PHX) to Chicago (ORD)

Delta • Non-stop • PremiumEconomy

Chicago (ORD) to Phoenix (PHX)

United • Non-stop • PremiumEconomy
Price was $1,368, price is now $1,112 per person
$1,112
per person
found 1 day ago
close to everything we will be staying here again on our next vacation to Chicago

Reviewed on Aug 31, 2024

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,716 reviews)

Nov 7 - Nov 11

4 night stay

Los Angeles (LAX) to Chicago (ORD)

Delta • Non-stop roundtrip • PremiumEconomy
Save 100% on your flight
Price was $1,793, price is now $1,287 per person
$1,287
per person
found 1 hour ago
Every employee makes every guest feel like a rockstar. Commitment to quality and guest experience is evident.

Reviewed on Sep 14, 2025

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Oakbrook Terrace 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! (2,427 reviews)

Oct 31 - Nov 2

2 night stay

Los Angeles (LAX) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,611, price is now $1,258 per person
$1,258
per person
found 12 hours ago
One day didn’t receive room service

Reviewed on Sep 2, 2025

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.4/10 Exceptional! (1,716 reviews)

Oct 31 - Nov 2

2 night stay

Los Angeles (LAX) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,800, price is now $1,447 per person
$1,447
per person
found 12 hours ago
Every employee makes every guest feel like a rockstar. Commitment to quality and guest experience is evident.

Reviewed on Sep 14, 2025

Park Hyatt Chicago
5.0-star property

Park Hyatt Chicago

9.6/10 Exceptional! (1,001 reviews)

Oct 31 - Nov 2

2 night stay

Los Angeles (LAX) to Chicago (ORD)

American Airlines • Roundtrip • FirstClass
Price was $1,794, price is now $1,499 per person
$1,499
per person
found 12 hours ago
From the moment you walk into their lobby at the hotel, you enter a place of calm and relaxation. We stayed in a room with the Water Tower view, and if you have that as the option, take it. It was a beautiful sight to see waking up every morning. This hotel like their other properties are in a class of their own.

Reviewed on Sep 13, 2024

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Oakbrook Terrace

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

Bargain Flights to Oakbrook Terrace

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Orbitz sends you free alerts and updates on your Oakbrook Terrace 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.

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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 Oakbrook Terrace 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 Oakbrook Terrace?
With 20 airlines providing services to O'Hare Intl. Airport (ORD), the main entry point to Oakbrook Terrace, you can take your pick. Grab an impressive deal among these renowned international airlines that'll take you to this city:

  • United Airlines - 612 flights to Oakbrook Terrace per month
  • American Airlines - 339 flights to Oakbrook Terrace per month
  • Air Canada - 190 flights to Oakbrook Terrace per month

What is the best airport to fly to in Oakbrook Terrace?
Hop on a plane to O'Hare Intl. Airport (ORD) and you'll be enjoying this awesome city in no time. This airport is approximately 9 miles north of the downtown area. But ORD isn't your only choice. Midway Intl. Airport (MDW) is another entry point to Oakbrook Terrace, so be sure to compare flight prices to get the best deal.
How much is a flight to Oakbrook Terrace?
Travelers from far and wide nabbed round-trip flight deals ranging between $49 and $137 this week to Oakbrook Terrace. Starting your journey from New York (EWR)? The most affordable one-way tickets were just $25.
How to book the cheapest flight to Oakbrook Terrace?
With some of the most competitive flight deals around, bagging a bargain is easy with Orbitz. The following pointers will help you find cheap flights to Oakbrook Terrace — and leave you with extra cash in your wallet:

  • Consider taking off from or landing at other airports to save extra cash. Enter your preferred departure and arrival airports in the form fields, then select the 'Nearby airports' function below. It will list any available options.
  • Also, click on the 'Show flexible dates' link to see the airfares on days around your selected departure. It's possible to score cheaper flight deals if you're flexible with your dates.
  • To refine your results, click on 'Show options.' You can search based on seating class, airlines, and nonstop and refundable flights. You can also choose the time of day you'd like to fly under 'Sort & Filter' to the left.
  • If you know your travel dates, don't delay booking your flight. Airfares generally become more expensive as the departure date nears.
  • Make greater savings on your trip by bundling your hotel, flights and car rentals into an Orbitz package. Your bank account will thank you.
  • Don't travel during the busy season if possible. By avoiding summer, school vacations and other popular dates, you can save loads on your airfares.

How long is a flight to Oakbrook Terrace?
Your point of origin, which airport you fly out of and whether your journey is direct — the flight duration depends on a lot of factors. But we've rounded up the average times for three of the most popular routes to Oakbrook Terrace:

  • 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 Oakbrook Terrace?
Land a bargain and secure your seats to Oakbrook Terrace in January. If you've missed this month, don't worry. February and August often have low airfares available. Be careful not to sleep on a sale though — cheap flights pop up and disappear in an instant!
What day of the week is the cheapest to book a flight to Oakbrook Terrace?
If you're after cheap fares to Oakbrook Terrace, the best days to book are Tuesdays, Wednesdays and Saturdays. With Orbitz (and some good timing!), a superb flight deal will be all yours.
What is the cheapest day of the week to fly to Oakbrook Terrace?
Think about going early in the week if you want to score cheap flights to Oakbrook Terrace. Orbitz data from 2020 shows Monday is typically the most inexpensive day to start your trip, followed by Tuesday. Saturday was found to have the highest airfares. Presumably, this is because most travelers prefer to begin their vacation at the end of the week.
What is the cheapest month to fly to Oakbrook Terrace?
Travel sometime in August if you're sticking to a budget. Orbitz data has found that it's generally the best month for cheap flights to Oakbrook Terrace. June is when airfares hit their peak.
Which airlines allow free cancellation?
Orbitz makes it a cinch to find carriers offering fare flexibility. Simply click on "Filter by flexible change policies" when searching for your flights and bada bing! You'll see options that include free cancellation, no change fees and of course, the very best price.
What do I need for the flight to Oakbrook Terrace?
Nothing's more enjoyable than flying off to a cool new destination, but it's good to be prepared. This list of practical tips will help get your trip off to a great start:

  • Your travel documents are the most important items you'll need to take on your flight. To avoid any dramas while checking in, make sure that the personal information on your ticket matches your government-issued photo ID.
  • To keep you occupied on the short trip to Oakbrook Terrace, download your favorite tunes or restock the audiobook library on your tablet. Food can also be a good distraction while in the air, so take some light snacks.
  • Even if you're flying when it's 90 degrees outside, bring a warm top or scarf on board with you. Cabins can get a bit chilly!

How many direct flights are there to Oakbrook Terrace?
Right now, there are 2,332 direct flights each month to Oakbrook Terrace. When it comes to airlines that will take you there, you're spoiled for choice. United Airlines, American Airlines and Delta Air Lines are some of the most popular. Southwest Airlines, Spirit Airlines and Air Canada are some other reliable carriers that offer nonstop services.
How do I get cheap first-class/business deals to Oakbrook Terrace?
Savvy travelers have a talent for finding first or business-class airfares to Oakbrook Terrace that don't cost a packet. Take their lead with these handy hints:

  • Be flexible with your travel dates and hold out for early bird or last-minute sales on first or business-class airfares.
  • Plenty of low-cost airlines these days offer quality business or premium-class seating for a wallet-friendly price.
  • Bid for an upgrade in online auctions (if available) or upgrade through your loyalty program.

How to get into Oakbrook Terrace from the airport?
Get off the plane at O'Hare Intl. Airport (ORD) and then grab the keys from one of the O'Hare Intl. Airport (ORD) car rental companies on-site, Thrifty Car Rental or Dollar. With your own sweet ride, getting to the downtown area of Oakbrook Terrace from ORD will be a cinch. Set your GPS and cruise 9 miles to the south. You could also use public transportation or take a taxi into town and rent a car directly from the city center. Check out the awesome deals available on our Oakbrook Terrace car rentals.
What is the best time to go to Oakbrook Terrace?
Oakbrook Terrace is a wonderful year-round vacation destination, but the most popular months to visit are May, June and July. If you're a fan of warmer weather, visit in summertime. Like most destinations in the Northern Hemisphere, the summer season kicks off June 20. Temperatures generally float between 65 ºF and 80 ºF during the day.
Travel tips for Oakbrook Terrace

  • The center of Oakbrook Terrace has plenty of superb attractions. Spots like Oakbrook Center Mall and Yorktown Shopping Center will keep your feet on the move and the sightseer in you satisfied.
  • If you're in the mood for an easy day trip, there are more sights to check off a short drive from the hustle and bustle. Discover why Wrigley Field and McCormick Place are on the bucket lists of many Oakbrook Terrace travelers.
  • Get your butt in the driver's seat and discover what else makes Chicago a magnet for travelers. Arrange a car rental with Orbitz and check out the delights of two other enticing cities — Gurnee and Waukegan.

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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.