Chicago

$50+ Cheap flights from Orlando (MCO) to Chicago (CHI)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/14. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Oct 15 — Oct 221
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Find cheap flights from Orlando to Chicago with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Orlando to Chicago are usually found in February or April, booked 46 days in advance, depart on a Friday or Thursday and return on a Tuesday

Cheap flight deals from Orlando to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Orlando (MCO) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated September 15, 2025.

Round-trip from

$87
(Cheapflightsfares)

One-way from

$50
(Cheapflightsfares)

Popular in

March

Cheapest in

February

Average price

$158

Good round-trip deal

$103 or less

Good one-way deal

$88 or less
From Orlando to Chicago (CHI)
One-way flight from Orlando to Chicago (CHI)
High demand for flights, 1% potential price rise
Cheapest flight prices on average. 3% potential price decrease ($7 potential savings vs. average RT price).
Average for round-trip flights in September 2025
Price to beat on a round-trip flight from Orlando to Chicago (CHI).
Price to beat on a one-way flight from Orlando to Chicago (CHI).

Find flight deals from Orlando to Chicago

Cheapest flights from Orlando to Chicago
Explore the most affordable flight options available from Orlando to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 15, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/25:24 pmMCO - ORD
Nonstop3h 20mFrontier
Sun 10/58:49 pmORD - MCO
Nonstop2h 46mFrontier
Deal found 9/13$87
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/32:07 pmMCO - ORD
Nonstop3h 05mMultiple Airlines
Sun 10/58:49 pmORD - MCO
Nonstop2h 46mMultiple Airlines
Deal found 9/13$88
This Frontier deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/271:02 pmMCO - ORD
Nonstop3h 15mFrontier
Mon 9/298:49 pmORD - MCO
Nonstop2h 46mFrontier
Deal found 9/14$89
This Mytrip deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/96:05 amMCO - ORD
Nonstop3h 09mMultiple Airlines
Tue 10/146:58 pmORD - MCO
Nonstop2h 52mMultiple Airlines
Deal found 9/13$90
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/35:24 pmMCO - ORD
Nonstop3h 20mFrontier
Sat 10/48:00 amORD - MCO
Nonstop2h 57mFrontier
Deal found 9/14$92
This Cheapflightsfares deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/111:16 pmMCO - MDW
Nonstop2h 55mFrontier
Sat 10/1811:31 amMDW - MCO
Nonstop2h 40mFrontier
Deal found 9/13$92
This Frontier deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/265:24 pmMCO - ORD
Nonstop3h 20mFrontier
Mon 9/298:49 pmORD - MCO
Nonstop2h 46mFrontier
Deal found 9/14$93
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/35:24 pmMCO - ORD
Nonstop3h 20mFrontier
Mon 10/68:49 pmORD - MCO
Nonstop2h 46mFrontier
Deal found 9/14$94
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/295:24 pmMCO - ORD
Nonstop3h 20mFrontier
Fri 10/38:49 pmORD - MCO
Nonstop2h 46mFrontier
Deal found 9/14$95
This Cheapflightsfares deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/37:00 amMCO - MDW
Nonstop2h 53mFrontier
Sun 10/510:13 amMDW - MCO
Nonstop2h 42mFrontier
Deal found 9/14$95
This Priceline deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/162:43 pmMCO - ORD
Nonstop3h 14mMultiple Airlines
Sun 10/196:00 amORD - MCO
Nonstop2h 44mMultiple Airlines
Deal found 9/14$96
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/307:50 pmMCO - ORD
Nonstop3h 08mSpirit Airlines
Tue 10/76:00 amORD - MCO
Nonstop2h 44mSpirit Airlines
Deal found 9/13$98

Cheapflights Fare Finder

 
Customize your flight search to find flights from Orlando to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
Use the filters below to find and compare flights from Orlando Airport to Chicago that are best for you.

Fly from

Orlando

Fly to

Chicago

Route

Depart

Return

Price

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 10/11

4:23 pm-6:33 pm

Nonstop3h 10m

Chicago O'Hare Intl

Mon 10/13

7:51 pm-11:43 pm

Nonstop2h 52m

$99

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 10/14

3:53 pm-5:53 pm

Nonstop3h 00m

Chicago O'Hare Intl

Tue 10/21

6:00 am-9:44 am

Nonstop2h 44m

$100

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 11/6

7:15 am-9:12 am

Nonstop2h 57m

Chicago Midway

Sat 11/8

6:30 am-1:54 pm

1 stop6h 24m

$112

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 10/23

7:50 am-9:47 am

Nonstop2h 57m

Chicago Midway

Sun 10/26

6:24 pm-5:53 am

1 stop10h 29m

$113

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 11/6

7:05 am-5:12 pm

1 stop11h 07m

Chicago O'Hare Intl

Mon 11/10

5:15 am-8:57 am

Nonstop2h 42m

$123

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 10/2

6:00 am-3:58 pm

1 stop10h 58m

Chicago Midway

Mon 10/6

8:19 am-12:00 pm

Nonstop2h 41m

$123

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 10/10

2:26 pm-4:20 pm

Nonstop2h 54m

Chicago Midway

Tue 10/14

8:05 am-6:52 pm

1 stop9h 47m

$124

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 10/11

1:16 pm-3:11 pm

Nonstop2h 55m

Chicago Midway

Tue 10/14

8:05 am-6:52 pm

1 stop9h 47m

$124

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sun 11/2

7:15 am-9:12 am

Nonstop2h 57m

Chicago Midway

Mon 11/3

9:32 am-1:14 pm

Nonstop2h 42m

$140

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 10/11

9:00 am-4:09 pm

1 stop8h 09m

Chicago Midway

Mon 10/13

5:28 pm-9:10 pm

Nonstop2h 42m

$143

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/13

Showing 1-10 of 57 results
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The best insider tips for Orlando Airport to Chicago flights

Snippets provided in this section are AI-generated based on a summarization of Cheapflights-commissioned articles. The articles are presented as-is, for general informational purposes only, and may not be up-to-date. The opinions contained in the articles are original to the author and reflect their authentic experience, which may vary significantly from the experience of others.
Cheapflights partnered with top experts to bring you the best recommendations for your Orlando Airport to Chicago trip
Airlines
British Airways

BA's World Traveller Plus offers extra seat width and legroom, ideal for comfort.


BA's Club Suite provides privacy with solo pods and a door you can close.

Frontier

Frontier's UpFront Plus seats guarantee an empty middle seat for more space.


Frontier's Economy Bundle includes a carry-on bag, seat selection, and no change fees.

Read more about Frontierby Marisa Garcia
Spirit Airlines

Spirit's Big Front Seats offer 11 inches more legroom and larger tray tables.


Spirit's self-service bag drop saves time; print your boarding pass beforehand to avoid charges.

Southwest

Southwest offers free snacks and non-alcoholic drinks, enhancing the low-cost travel experience.


Southwest's Early Bird check-in ensures priority boarding, ideal for business travelers.

United Airlines

Basic Economy allows only a personal item; no carry-on bags unless exceptions apply.


Economy Plus offers extra legroom seats at the front of the economy cabin.

Airports
MCO

Use MCO Reserve to pre-book a security line slot, saving time during busy periods. Book up to a week in advance.

Read more about MCOby Paul Rubio
ORD

Take the “L” train from ORD to downtown Chicago for a cost-effective and reliable transport option.

Read more about ORDby Ramsey Qubein
MDW

Use the Orange Line train from MDW for a quick, 30-minute ride to downtown Chicago.

Read more about MDWby Ramsey Qubein
Our travel experts
Gabriel Leigh

Gabriel Leigh

Expert on British Airways

Gabriel Leigh

Gabriel Leigh

Gabriel is a writer and video creator. As senior content producer for Flightradar24 and Monocle’s transport correspondent, he keeps a close eye on aviation in particular. He has also written travel articles for the likes of The New York Times. Born in New York but raised around the world, he now lives in Sweden. He’s been to 75 countries, flying 2.3 million miles on 113 airlines and through 234 airports in the process.

Read more
Marisa Garcia

Marisa Garcia

Expert on Frontier and Southwest

Marisa Garcia

Marisa Garcia

Marisa knows planes inside and out, spending 16 years working on aircraft in hangars at airports around the world. She is an aviation industry expert, specialized in airline interiors and regulations. Ten years ago, she pivoted to journalism. She shares her insights in leading aviation, travel, and business publications and on her site FlightChic.

Read more
Daniel Scheffler

Daniel Scheffler

Expert on Spirit Airlines

Daniel Scheffler

Daniel Scheffler

Daniel Scheffler is a travel writer, podcaster, and producer. Born in Africa, bred in Europe and now living in America he has traveled to 140 countries (and all 50 U.S. states). Plus he has stayed at over 2500 hotels across the globe. His original shows Everywhere and Without Maps (available on Spotify) showcase his beliefs, travel is about humanity and sharing that beauty. And thus it reminds you that you shouldn’t believe everything you think.

Read more
Harriet Baskas

Harriet Baskas

Expert on United Airlines

Harriet Baskas

Harriet Baskas

Harriet is an award-winning journalist who is happiest in an airport or an unusual museum. Her stories about airports, air travel, and the business of travel have appeared on NBC News, CNBC, USA TODAY, The Points Guy and other outlets. She is the creator of the StuckatTheAirport.com blog and the author of nine books. When not out on the road or exploring the latest airport amenities, she’s home in Seattle getting ready for the next adventure.

Read more
Ramsey Qubein

Ramsey Qubein

Expert on ORD and MDW

Ramsey Qubein

Ramsey Qubein

An avid traveler and aviation expert who has visited 173 countries, all 50 states and seven continents, Ramsey Qubein flies nearly 400,000 miles a year. As a North Carolina-based freelance journalist for publications including Conde Nast Traveler, Forbes, USA Today and Bloomberg among others, he explores the latest trends in aviation, hospitality, cruises and business.

Read more
Paul Rubio

Paul Rubio

Expert on MCO

Paul Rubio

Paul Rubio

Travel journalist and photographer Paul Rubio is a Miami native (and current resident), who has lived in nine countries and traveled to 137. He is an expert in luxury travel, eco-travel, loyalty programs, hotels, airports and airlines. He is a contributing editor at AFAR, Condé Nast Traveler, LUXURY Magazine, and Palm Beach Illustrated.

Read more

Best time to book a flight from Orlando to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Orlando with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Orlando Airport to Chicago

How far ahead should I book a flight from Orlando Airport to Chicago?

Use this chart to determine the optimal time to book a round-trip flight from Orlando to Chicago. Price data was last updated on September 12, 2025.

The best time to book flights from Orlando Airport to Chicago is 46 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

What is the cheapest month to book a flight from Orlando Airport to Chicago?

Currently, August is the cheapest month in which you can book a flight from Orlando Airport to Chicago (average of $245). Flying from Orlando Airport to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from MCO to CHI?

Find hourly flight availability from Orlando to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 15, 2025.

It’s typically best to fly out from Orlando Airport to Chicago in the evening. Doing so could potentially save you 59% on the flight price compared to flying at noon, which is usually more expensive.

What is the cheapest day to fly from Orlando Airport to Chicago?

Use this chart to determine the cheapest time to fly round-trip from Orlando to Chicago. Price data was last updated on September 7, 2025.

Travelers seeking maximum savings on their Orlando Airport to Chicago flight should consider departing on Thursday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Weekly flight availability from Orlando Airport to Chicago

Explore weekly flight availability from Orlando to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 15, 2025.

The most flights from MCO to CHI are scheduled on a Sunday (75 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (44 on average).

Reviews of airlines servicing Chicago

Get insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated September 15, 2025.
See what other customers who have flown with Southwest, United Airlines, and American Airlines from Orlando Airport to Chicago have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Related info for your journey

Find useful and relevant information for your journey from Orlando to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • How long is the flight from Orlando Airport to Chicago?

    For as low as $112, Spirit Airlines can have you in Chicago from Orlando Airport in 2h 57m. There are 990 mi between Orlando Airport and Chicago. Generally, flights for this route are nonstop.

  • What are the cheapest airlines flying from Orlando Airport to Chicago round-trip?

    Currently priced at $72, Frontier will fly you from Orlando Airport to Chicago and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Spirit Airlines and Delta - these airlines can fly you to your destination from $73 and $114, respectively. Users have found that Frontier is 63% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Orlando Airport to Chicago one-way?

    The cheapest airlines for a one-way flight from Orlando Airport to Chicago are Spirit Airlines ($50), Frontier ($58), and Southwest ($67).

  • What are the most popular routes from Orlando Airport to Chicago?

  • What are the most reliable airlines from Orlando Airport to Chicago?

    No one likes to see their flight delayed. When booking a flight from Orlando Airport to Chicago consider choosing Brussels Airlines (80%), Cathay Pacific (79%) or United Airlines (78%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Orlando Airport to Chicago?

    Looking at all options, your cheapest flight can be booked for $54. While the most popular route (Orlando - Chicago O'Hare Intl) can be booked for $86 on average, our data indicates $1,117 when flying from Orlando Airport to Chicago.

  • Can I find deals for flights from Orlando to Chicago that include hotel bookings?

    Yes. In addition to deals on Orlando to Chicago flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Orlando to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Orlando to Chicago.

  • Can I find deals for business class flights from Orlando to Chicago?

    Yes. Cheapflights offers flight deals from Orlando to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Orlando Airport to Chicago?

    Currently, August is the cheapest month in which you can book a flight from Orlando Airport to Chicago (average of $245). Flying from Orlando Airport to Chicago in March is currently the most expensive (average of $321). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Lansing
Hammond
Benton Harbor
Porter
Chesterton

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Top 6 airlines flying from Orlando to Chicago

Discover the top 6 airlines that operate flights from Orlando to Chicago. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated September 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$170FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$73Average$140FlexibilityNo cancel feeOn-time65%
DeltaCheapest$114Average$332FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$158Average$346FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$277FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$159Average$298FlexibilityNo cancel feeOn-time63%

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