HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Chicago

$56+ 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 8/15. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
ago. 4 — ago. 111
lun. 8/4
lun. 8/11
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Orlando to Chicago are usually found in September or February, booked 75 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 julio 30, 2025.

Round-trip from

$105
(Kiwi.com)

One-way from

$55
(Cheapflightsfares)

Popular in

March

Cheapest in

September

Average price

$196

Good round-trip deal

$158 or less

Good one-way deal

$104 or less
From Orlando to Chicago (CHI)
Search Deals
One-way flight from Orlando to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 0% potential increase in price ($0 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2025
Search Deals
Price to beat on a round-trip flight from Orlando to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Orlando to Chicago (CHI).
Search Deals

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 julio 30, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/142:07 pmMCO - ORD
Nonstop3h 05mSpirit Airlines
mié. 10/226:30 amORD - MCO
Nonstop2h 43mSpirit Airlines
Deal found 7/28$105
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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.
vie. 8/226:30 amMCO - MDW
Nonstop2h 52mFrontier
lun. 8/254:24 pmMDW - MCO
Nonstop2h 50mFrontier
Deal found 7/29$106
This Cheapflightsfares deal was found by Cheapflights users on 7/29. 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.
mar. 8/58:00 amMCO - ORD
Nonstop3h 14mFrontier
mar. 8/1211:28 amORD - MCO
Nonstop2h 59mFrontier
Deal found 7/29$107
This Kiwi.com deal was found by Cheapflights users on 7/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/159:18 pmMCO - ORD
Nonstop3h 13mMultiple Airlines
lun. 8/186:56 amORD - MCO
Nonstop2h 38mMultiple Airlines
Deal found 7/28$117
This Southwest deal was found by Cheapflights users on 7/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 8/303:35 pmMCO - MDW
Nonstop2h 45mSouthwest
mar. 9/24:45 pmMDW - MCO
Nonstop2h 40mSouthwest
Deal found 7/30$157
This Mytrip deal was found by Cheapflights users on 7/28. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/178:35 amMCO - RFD
1 stop11h 23mMultiple Airlines
lun. 10/273:03 pmRFD - MCO
1 stop6h 59mMultiple Airlines
Deal found 7/28$170

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 julio 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 - ORD

MCOORD

Orlando

mar. 10/14

2:07 pm-4:12 pm

Nonstop3h 05m

Chicago O'Hare Intl

mié. 10/22

6:30 am-10:13 am

Nonstop2h 43m

$105

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

vie. 8/22

6:30 am-8:22 am

Nonstop2h 52m

Chicago Midway

lun. 8/25

4:24 pm-8:14 pm

Nonstop2h 50m

$106

OrlandoChicago

MCO - ORD

MCOORD

Orlando

mar. 8/5

8:00 am-10:14 am

Nonstop3h 14m

Chicago O'Hare Intl

mar. 8/12

11:28 am-3:27 pm

Nonstop2h 59m

$107

OrlandoChicago

MCO - ORD

MCOORD

Orlando

vie. 8/15

9:18 pm-11:31 pm

Nonstop3h 13m

Chicago O'Hare Intl

lun. 8/18

6:56 am-10:34 am

Nonstop2h 38m

$117

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

sáb. 8/30

3:35 pm-5:20 pm

Nonstop2h 45m

Chicago Midway

mar. 9/2

4:45 pm-8:25 pm

Nonstop2h 40m

$157

OrlandoChicago

MCO - RFD

MCORFD

Orlando

vie. 10/17

8:35 am-6:58 pm

1 stop11h 23m

Chicago Greater Rockford

lun. 10/27

3:03 pm-11:02 pm

1 stop6h 59m

$170

OrlandoChicago

MCO - ORD

MCOORD

Orlando

vie. 8/15

2:07 pm-4:10 pm

Nonstop3h 03m

$56

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

lun. 9/8

5:35 am-7:23 am

Nonstop2h 48m

$56

OrlandoChicago

MCO - ORD

MCOORD

Orlando

mié. 8/6

8:00 am-10:14 am

Nonstop3h 14m

$59

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

mar. 10/28

7:20 am-9:10 am

Nonstop2h 50m

$79

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

Showing 1-10 of 16 results
1
2

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
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

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 July 25, 2025.

The best time to book flights from Orlando Airport to Chicago is 75 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 julio 30, 2025.

It’s typically best to fly out from Orlando Airport to Chicago in the evening. Doing so could potentially save you 63% 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 July 27, 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. Wednesday 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 julio 30, 2025.

The most flights from MCO to CHI are scheduled on a Monday (71 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (27 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 julio 30, 2025.
See what other customers who have flown with Southwest, Delta, 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
4,241 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

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.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

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.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

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.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

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.
Allegiant Air
7.2
Good
703 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

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.
Spirit Airlines
6.3
Okay
8,048 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

Crew

8.6

Overall

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.

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

    Currently priced at $105, Spirit Airlines will fly you from Orlando Airport to Chicago and back. In addition to Spirit Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Frontier and Southwest - these airlines can fly you to your destination from $106 and $157, respectively. Users have found that Spirit Airlines is 45% 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 Frontier ($55), Spirit Airlines ($56), and Southwest ($79).

  • 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 Brussels Airlines (93%), Austrian Airlines (93%) or Cathay Pacific (88%) 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 $64. While the most popular route (Orlando - Chicago O'Hare Intl) can be booked for $79 on average our data indicates $2,179 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
Valparaiso
Chesterton

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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 julio 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$72Average$155FlexibilityNo cancel feeOn-time65%
FrontierCheapest$73Average$172FlexibilityNo cancel feeOn-time62%
DeltaCheapest$114Average$346FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$157Average$339FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$280FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$165Average$322FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.