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$52+ 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 12/15. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Find cheap flights from Orlando to Chicago with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

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3. Compare prices and book

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Cheapflights Tip: The best prices from Orlando to Chicago are usually found in February or September, booked 50 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 October 30, 2025.

Most accurate provider

Justfly.com
3 stars

Most trusted provider

Justfly.com
3 stars

Round-trip from

$81
(Kiwi.com)

One-way from

$52
(Cheapflightsfares)

Popular in

March

Cheapest in

February

Average price

$195

Good round-trip deal

$114 or less

Good one-way deal

$95 or less
Provider with most accurate pricing for Orlando-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Orlando-Chicago (CHI) flights.
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From Orlando to Chicago (CHI)
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One-way flight from Orlando to Chicago (CHI)
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High demand for flights, 1% potential price rise
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Cheapest flight prices on average. 3% potential price decrease ($6 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Price to beat on a round-trip flight from Orlando to Chicago (CHI).
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Price to beat on a one-way flight from Orlando to Chicago (CHI).
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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 October 30, 2025.

This CheapOair deal was found by Cheapflights users on 10/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/227:46 pmMCO - ORD
Nonstop3h 11mFrontier
Mon 11/246:15 pmORD - MCO
Nonstop3h 04mFrontier
Deal found 10/28$80
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Thu 11/139:00 pmMCO - ORD
Nonstop3h 06mMultiple Airlines
Sun 11/165:25 amORD - MCO
Nonstop2h 42mMultiple Airlines
Deal found 10/29$81
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/78:24 pmMCO - MDW
Nonstop2h 56mFrontier
Sun 11/910:12 amMDW - MCO
Nonstop2h 38mFrontier
Deal found 10/29$81
This Cheapflightsfares deal was found by Cheapflights users on 10/29. 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 11/710:17 amMCO - ORD
Nonstop3h 09mFrontier
Sun 11/95:25 amORD - MCO
Nonstop2h 42mFrontier
Deal found 10/29$82
This Frontier deal was found by Cheapflights users on 10/28. 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 11/1510:30 amMCO - ORD
1 stop7h 43mFrontier
Mon 11/175:15 amORD - MCO
Nonstop2h 42mFrontier
Deal found 10/28$83
This Orbitz deal was found by Cheapflights users on 10/27. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/57:15 pmMCO - ORD
Nonstop3h 04mSpirit Airlines
Sun 12/712:09 pmORD - MCO
Nonstop2h 52mSpirit Airlines
Deal found 10/27$84
This Priceline deal was found by Cheapflights users on 10/30. 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.
Fri 11/148:14 pmMCO - MDW
Nonstop2h 56mFrontier
Sat 11/156:30 amMDW - MCO
1 stop6h 24mFrontier
Deal found 10/30$84
This Frontier deal was found by Cheapflights users on 10/28. 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 11/710:17 amMCO - ORD
Nonstop3h 09mFrontier
Mon 11/105:15 amORD - MCO
Nonstop2h 42mFrontier
Deal found 10/28$85
This CheapOair deal was found by Cheapflights users on 10/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/67:15 amMCO - MDW
Nonstop2h 57mFrontier
Mon 11/108:00 amMDW - MCO
Nonstop2h 41mFrontier
Deal found 10/29$85
This Priceline deal was found by Cheapflights users on 10/30. 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.
Wed 11/199:00 pmMCO - ORD
Nonstop3h 06mMultiple Airlines
Thu 11/206:23 pmORD - MCO
Nonstop3h 04mMultiple Airlines
Deal found 10/30$86
This Cheapflightsfares deal was found by Cheapflights users on 10/28. 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 11/139:00 pmMCO - ORD
Nonstop3h 06mSpirit Airlines
Mon 11/176:48 amORD - MCO
Nonstop2h 42mSpirit Airlines
Deal found 10/28$87
This Frontier deal was found by Cheapflights users on 10/30. 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.
Mon 11/176:35 amMCO - MDW
Nonstop2h 57mFrontier
Fri 11/284:46 pmMDW - MCO
Nonstop2h 48mFrontier
Deal found 10/30$87

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 October 30, 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 - MDW

MCOMDW

Orlando

Wed 12/31

7:58 pm-9:58 pm

Nonstop3h 00m

Chicago Midway

Sat 1/3

2:16 pm-6:01 pm

Nonstop2h 45m

$97

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Mon 12/22

7:58 pm-9:58 pm

Nonstop3h 00m

Chicago Midway

Wed 12/31

3:10 pm-6:58 pm

Nonstop2h 48m

$97

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 12/9

5:27 pm-10:11 pm

1 stop5h 44m

Chicago O'Hare Intl

Sat 12/13

7:20 am-11:12 am

Nonstop2h 52m

$109

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 11/22

9:54 am-6:26 pm

1 stop9h 32m

Chicago O'Hare Intl

Sun 11/23

11:23 am-3:15 pm

Nonstop2h 52m

$122

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sun 11/16

7:15 am-9:12 am

Nonstop2h 57m

Chicago Midway

Fri 11/28

4:46 pm-8:34 pm

Nonstop2h 48m

$136

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 2/19

12:12 pm-2:29 pm

Nonstop3h 17m

Chicago O'Hare Intl

Sun 2/22

7:50 pm-11:43 pm

Nonstop2h 53m

$137

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Mon 12/22

7:58 pm-9:58 pm

Nonstop3h 00m

Chicago Midway

Mon 12/29

3:10 pm-6:58 pm

Nonstop2h 48m

$138

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Mon 11/17

5:40 am-5:01 pm

1 stop12h 21m

Chicago Midway

Fri 11/28

4:46 pm-8:34 pm

Nonstop2h 48m

$144

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 2/25

2:00 pm-4:17 pm

Nonstop3h 17m

Chicago O'Hare Intl

Wed 3/4

3:41 pm-7:31 pm

Nonstop2h 50m

$147

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 12/9

10:30 am-12:33 pm

Nonstop3h 03m

Chicago O'Hare Intl

Tue 12/9

2:10 pm-6:01 pm

Nonstop2h 51m

$152

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/28

Showing 1-10 of 57 results
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Compare providers for flights from Orlando to Chicago

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Orlando to Chicago in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*1 star
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
CheapfaremartPrice Accuracy-Trust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Orlando Airport-Chicago flights, users find the pricing of Justfly.com to be most consistent on Cheapflights vs. Justfly.com Users can find the same prices on Orlando Airport-Chicago flight deals on Cheapflights vs. Justfly.com >95% of the time. Price accuracy is based on data collected from Orlando Airport-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Orlando Airport-Chicago flights, Cheapflights users trust Justfly.com the most. Justfly.com has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Orlando Airport-Chicago flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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 October 24, 2025.

The best time to book flights from Orlando Airport to Chicago is 50 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, November is the cheapest month in which you can book a flight from Orlando Airport to Chicago (average of $54). Flying from Orlando Airport to Chicago in June is currently the most expensive (average of $113). 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 October 30, 2025.

It’s typically best to fly out from Orlando Airport to Chicago in the evening. Doing so could potentially save you 43% 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 October 26, 2025.

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

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.

Read more about British Airwaysby Gabriel Leigh
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.

Read more about Spirit Airlinesby Daniel Scheffler
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.

Read more about Southwestby Marisa Garcia
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.

Read more about United Airlinesby Harriet Baskas
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

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 October 30, 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.
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Crew

8.6

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.
Southwest
8.0
Very good
4,243 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Crew

8.6

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.
United Airlines
7.4
Good
8,998 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Crew

8.6

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.
American Airlines
7.2
Good
11,035 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Crew

8.6

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.
Spirit Airlines
6.3
Okay
8,116 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Crew

8.6

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.
Frontier
5.8
Fair
3,122 reviews
Southwest
8.0
Very good
4,243 reviews

Food

7.0

Boarding

8.1

Comfort

8.0

Overall

8.0

Entertainment

7.5

Crew

8.6

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 $97, Frontier can have you in Chicago from Orlando Airport in 3h. There are 990 mi between Orlando Airport and Chicago. Both multi-stop and nonstop flights can be found to your destination and back.

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

    Currently priced at $69, 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 $74 and $114, respectively. Users have found that Frontier is 64% cheaper than the other options available to this destination.

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

    The most popular route from Orlando Airport to Chicago is Orlando - Chicago O'Hare Intl. You may also consider Orlando - Chicago Midway or Orlando - Chicago Greater Rockford.

  • 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 ITA Airways (97%), Japan Airlines (87%) or SWISS (86%) 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 $43. While the most popular route (Orlando - Chicago O'Hare Intl) can be booked for $71 on average, our data indicates $852 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, November is the cheapest month in which you can book a flight from Orlando Airport to Chicago (average of $54). Flying from Orlando Airport to Chicago in June is currently the most expensive (average of $113). 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
Porter
Benton Harbor

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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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$69Average$172FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$74Average$139FlexibilityNo cancel feeOn-time65%
DeltaCheapest$114Average$332FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$157Average$315FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$281FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$159Average$295FlexibilityNo cancel feeOn-time63%

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