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Compare Cheap Flights from Orlando to Chicago

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Round Trip Flights from Orlando to Chicago

16 May
MCO
20 May
ORD
$ 91.94
01 May
MCO
05 May
ORD
$ 114.96
16 May
MCO
20 May
ORD
$ 150.45
11 May
MCO
19 May
ORD
$ 187.97
02 Jun
MCO
06 Jun
ORD
$ 193.17
08 May
MCO
15 May
ORD
$ 216.39
*Note: All fares are quoted in USD.

Last updated on Friday 04/18/2025 at 05:00 AM, the fares mentioned above are for flight tickets and inclusive of fuel surcharges, service fee and taxes. Based on historical data, these fares are subject to change without prior notice and cannot be guaranteed at the time of booking. Kindly go through our terms and conditions before booking.

Book Orlando To Chicago Flights

Thinking of a vacation in Chicago? Well, there are many reasons why this city in Illinois is one of the most spectacular places to visit. Starting with the skyline, Chicago holds the top rank of the city with the tallest skyline in the world. It consists of America's eight tallest buildings and the famous Willis Tower. Reach the top at the Skydeck from where one can witness the breathtaking views of the city. 

Chicago is blessed with dynamic architecture that has a perfect fusion of modern buildings and impressive ancient architecture. Most of the buildings here reflect the Neoclassical, Châteauesque, and Chicago School, or the Commercial Style. Rockefeller Memorial Chapel, the Chicago Cultural Center, and the Rookery Building are a few impressive examples of architectural marvels of Chicago. The culture of Chicago is diverse where you will find everything: art, history, and music. Chicago-style jazz and rock and roll are the two main music forms you will hear in almost every corner of the city. There are museums such as Field Museum, Griffin Museum of Science and Industry, Museum Of Contemporary Art Chicago, and Institute for the Study of Ancient Cultures Museum preserving the rich art and history. 

From Chicago-style pizza to boating in Lake Michigan, the city promises an experience like never before. Book your Flights from Orlando to Chicago now to discover the best of the city's culture, food scene, and art. Flights to Chicago operate from both the airports- Orlando International Airport (MCO) and Orlando Sanford International Airport (SFB). There are two airports in Chicago- Chicago O'Hare International Airport (ORD) and Chicago Midway International Airport (MDW). Compare the airfare and book cheap flights to Chicago from Orlando. United, Southwest, Spirit, and Frontier are a few popular airlines that operate regular flights to Chicago from Orlando. 

If you have any questions regarding ORL to CHI flights, give us a call. We have a team of experts available 24/7 to assist users with cheap flight bookings, deals, and offers.
 

Finding Cheap Flights From Orlando To Chicago : Frequently Asked Questions

* The mentioned flight facts are based on the last 3 months' data. Information regarding the highest and lowest booking months is based on the last 12 months' data.

Major Carriers Operating Flights From Orlando To Chicago
Airline Cheapest Average

SPIRIT AIRLINES $49 $129

UNITED AIRLINES $123 $242

AMERICAN AIRLINES $88 $260

Low Cost Carriers Operating Flights From Orlando To Chicago
Airline Cheapest Average

SPIRIT AIRLINES $49 $129

FRONTIER AIRLINES $50 $151

AMERICAN AIRLINES $88 $260

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