Chicago

$58+ 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 4/26. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Apr 8 — Apr 151
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 April or May, booked 76 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 April 3, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$88
(eDestinos)

One-way from

$58
(Cheapflightsfares)

Popular in

December

Cheapest in

April

Average price

$145

Good round-trip deal

$155 or less

Good one-way deal

$107 or less
Provider with most accurate pricing for Orlando-Chicago (CHI) flight deals.
Provider most trusted by Cheapflights users for Orlando-Chicago (CHI) flights.
From Orlando to Chicago (CHI)
One-way flight from Orlando to Chicago (CHI)
Highest demand for flights based on searches. 11% potential increase in price ($23 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($3 potential savings vs. average RT price).
Average for round-trip flights in April 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 April 3, 2025.

This eDestinos deal was found by Cheapflights users on 4/2. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/176:00 amMCO - ORD
Nonstop3h 04mSpirit Airlines
Sun 4/208:45 amORD - MCO
Nonstop2h 47mSpirit Airlines
Deal found 4/2$88
This Kiwi.com deal was found by Cheapflights users on 4/2. 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 4/154:45 pmMCO - ORD
Nonstop3h 19mMultiple Airlines
Sun 4/208:45 amORD - MCO
Nonstop2h 47mMultiple Airlines
Deal found 4/2$94
This Frontier deal was found by Cheapflights users on 4/2. 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 4/116:30 amMCO - ORD
Nonstop3h 19mFrontier
Sat 4/127:20 amORD - MCO
Nonstop2h 53mFrontier
Deal found 4/2$100
This eDestinos deal was found by Cheapflights users on 4/2. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/177:25 amMCO - MDW
Nonstop2h 59mFrontier
Sat 4/1912:58 pmMDW - MCO
Nonstop2h 53mFrontier
Deal found 4/2$100
This Southwest deal was found by Cheapflights users on 4/2. 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.
Wed 5/711:00 amMCO - ORD
Nonstop3h 05mSouthwest
Sat 5/104:00 pmORD - MCO
Nonstop2h 50mSouthwest
Deal found 4/2$177
This Southwest deal was found by Cheapflights users on 4/2. 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.
Wed 5/78:00 amMCO - MDW
Nonstop2h 50mSouthwest
Sat 5/106:40 pmMDW - MCO
Nonstop2h 35mSouthwest
Deal found 4/2$177
This American Airlines deal was found by Cheapflights users on 4/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/76:52 amMCO - ORD
Nonstop3h 07mAmerican Airlines
Sun 5/117:10 amORD - MCO
Nonstop2h 40mAmerican Airlines
Deal found 4/3$178
This United Airlines deal was found by Cheapflights users on 4/2. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/259:32 amMCO - ORD
Nonstop3h 07mUnited Airlines
Wed 5/289:15 amORD - MCO
Nonstop2h 55mUnited Airlines
Deal found 4/2$179
This Delta deal was found by Cheapflights users on 4/2. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2011:00 amMCO - MDW
1 stop5h 20mDelta
Sun 5/259:16 amMDW - MCO
1 stop6h 38mDelta
Deal found 4/2$198
This Delta deal was found by Cheapflights users on 4/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/244:45 pmMCO - ORD
1 stop7h 32mDelta
Sun 5/2510:30 amORD - MCO
1 stop5h 24mDelta
Deal found 4/3$199
This Mytrip deal was found by Cheapflights users on 4/1. 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 5/296:17 amMCO - RFD
1 stop10h 07mMultiple Airlines
Sun 6/14:16 pmRFD - MCO
1 stop27h 27mMultiple Airlines
Deal found 4/1$207
This Mytrip deal was found by Cheapflights users on 4/1. 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 5/299:42 pmMCO - MDW
2 stops22h 32mMultiple Airlines
Mon 6/28:04 pmMDW - MCO
2 stops23h 33mMultiple Airlines
Deal found 4/1$291

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 April 3, 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

Thu 4/17

6:00 am-8:04 am

Nonstop3h 04m

Chicago O'Hare Intl

Sun 4/20

8:45 am-12:32 pm

Nonstop2h 47m

$88

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 4/15

4:45 pm-7:04 pm

Nonstop3h 19m

Chicago O'Hare Intl

Sat 4/19

11:45 am-3:31 pm

Nonstop2h 46m

$94

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 4/18

6:30 am-8:49 am

Nonstop3h 19m

Chicago O'Hare Intl

Sun 4/20

9:25 am-1:21 pm

Nonstop2h 56m

$100

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 4/17

7:25 am-9:24 am

Nonstop2h 59m

Chicago Midway

Sat 4/19

12:58 pm-4:51 pm

Nonstop2h 53m

$100

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 5/7

11:00 am-1:05 pm

Nonstop3h 05m

Chicago O'Hare Intl

Sat 5/10

4:00 pm-7:50 pm

Nonstop2h 50m

$177

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 5/7

6:52 am-8:59 am

Nonstop3h 07m

Chicago O'Hare Intl

Sun 5/11

7:10 am-10:50 am

Nonstop2h 40m

$178

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 4/29

2:00 pm-3:50 pm

Nonstop2h 50m

Chicago Midway

Tue 5/6

5:55 am-9:25 am

Nonstop2h 30m

$178

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sun 5/25

9:32 am-11:39 am

Nonstop3h 07m

Chicago O'Hare Intl

Wed 5/28

9:15 am-1:10 pm

Nonstop2h 55m

$179

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 5/24

4:45 pm-11:17 pm

1 stop7h 32m

Chicago O'Hare Intl

Sun 5/25

10:30 am-4:54 pm

1 stop5h 24m

$199

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 4/23

6:05 am-12:35 pm

1 stop7h 30m

Chicago Midway

Wed 4/23

5:59 pm-11:16 pm

1 stop4h 17m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/2

Showing 1-10 of 27 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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy3 starsTrust Score*2 stars
PricelinePrice Accuracy1 starTrust Score*3 stars
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
JustAirTicketPrice Accuracy-Trust Score*3 stars
FlightnetworkPrice Accuracy-Trust Score*3 stars
Kiwi.comPrice Accuracy3 starsTrust Score*2 stars

*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 FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Orlando Airport-Chicago flight deals on Cheapflights vs. FlightHub >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 FlightHub the most. FlightHub 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.

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.

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

Check real-time security wait times on MCO's website or app to plan your arrival and avoid long lines.

Read more about MCOby Paul Rubio
ORD

Use the free shuttle train at ORD to navigate between terminals and avoid long walks.

Read more about ORDby Ramsey Qubein
MDW

Take the 'L' train from MDW for a quick, affordable ride to downtown Chicago in under 30 minutes.

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 March 28, 2025.

The best time to book flights from Orlando Airport to Chicago is 76 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 April 3, 2025.

It’s typically best to fly out from Orlando Airport to Chicago in the evening. Doing so could potentially save you 79% 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 March 30, 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 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 April 3, 2025.

The most flights from MCO to CHI are scheduled on a Thursday (73 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (28 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 1.7 - 4.9 inches per month. August is typically the wettest month, when rainfall can reach 4.9 in. January is typically the driest time to visit Chicago when rainfall is around 1.7 in.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 April 3, 2025.
Get a feel of what it's like to fly with Alaska Airlines, Southwest and Delta from Orlando to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Boarding

8.2

Entertainment

7.1

Food

7.1

Crew

8.5

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Boarding

8.2

Entertainment

7.1

Food

7.1

Crew

8.5

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Boarding

8.2

Entertainment

7.1

Food

7.1

Crew

8.5

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them
8.0
Very good

Boarding

8.2

Entertainment

7.1

Food

7.1

Crew

8.5

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Boarding

8.2

Entertainment

7.1

Food

7.1

Crew

8.5

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

Boarding

8.2

Entertainment

7.1

Food

7.1

Crew

8.5

Comfort

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Cheri,Jan 2025

FAT - SEA

Very friendly. I really liked that they had water for us in cartons not plastic. Impressed with Alaska Airlines, First time I had flown them

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 $88, 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 $100 and $177, respectively. Users have found that Spirit Airlines is 52% 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 ($58), Spirit Airlines ($60), and United Airlines ($89).

  • 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 Japan Airlines (95%), Austrian Airlines (92%) or Brussels Airlines (90%) 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 $55. While the most popular route (Orlando - Chicago O'Hare Intl) can be booked for $75 on average our data indicates $2,357 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 Orlando Airport?

Book flights to Orlando Airport if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
Valparaiso
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 April 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$64Average$163FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$68Average$164FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$156Average$330FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$159Average$285FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$184Average$395FlexibilityNo cancel feeOn-time63%
DeltaCheapest$227Average$307FlexibilityNo cancel feeOn-timeN/A

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