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$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 2/14. Fares are subject to change and may not be available on all flights or dates of travel.
MCO — CHI
Feb 4 — Feb 111
Tue 2/4
Tue 2/11
1 adult, Economy
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The best prices from Orlando to Chicago are usually found in February or April, booked 89 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 January 30, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$93
(Cheapflightsfares)

One-way from

$58
(FlightHub)

Popular in

June

Cheapest in

February

Average price

$193

Good round-trip deal

$138 or less

Good one-way deal

$132 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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Highest demand for flights based on searches. 7% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
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Average for round-trip flights in January 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 January 30, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 1/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/142:41 pmMCO - ORD
Nonstop3h 08mSpirit Airlines
Sun 2/1612:48 pmORD - MCO
1 stop9h 41mSpirit Airlines
Deal found 1/30$93
This Frontier deal was found by Cheapflights users on 1/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/65:32 pmMCO - MDW
Nonstop3h 03mFrontier
Mon 3/106:38 pmMDW - MCO
1 stop5h 00mFrontier
Deal found 1/29$93
This Frontier deal was found by Cheapflights users on 1/29. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/275:05 amMCO - ORD
Nonstop3h 04mFrontier
Thu 3/611:55 amORD - MCO
1 stop11h 43mFrontier
Deal found 1/29$94
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 2/146:16 pmMCO - ORD
1 stop6h 42mMultiple Airlines
Sun 2/168:14 amORD - MCO
Nonstop3h 01mMultiple Airlines
Deal found 1/29$98
This Kissandfly.com deal was found by Cheapflights users on 1/30. 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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/65:07 amMCO - MDW
2 stops14h 19mMultiple Airlines
Sun 2/910:58 amMDW - MCO
Nonstop2h 47mMultiple Airlines
Deal found 1/30$167
This Delta deal was found by Cheapflights users on 1/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/275:30 amMCO - MDW
1 stop7h 29mDelta
Sun 3/25:05 pmMDW - MCO
1 stop6h 30mDelta
Deal found 1/29$204
This Southwest deal was found by Cheapflights users on 1/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/286:20 amMCO - ORD
1 stop8h 40mSouthwest
Mon 3/311:25 amORD - MCO
2 stops7h 20mSouthwest
Deal found 1/29$216
This Southwest deal was found by Cheapflights users on 1/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/265:45 pmMCO - MDW
Nonstop3h 00mSouthwest
Tue 3/410:25 amMDW - MCO
Nonstop2h 40mSouthwest
Deal found 1/29$257
This Mytrip deal was found by Cheapflights users on 1/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/198:45 amMCO - RFD
2 stops26h 58mMultiple Airlines
Mon 3/3111:33 amRFD - MCO
2 stops20h 22mMultiple Airlines
Deal found 1/29$458
This Mytrip deal was found by Cheapflights users on 1/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/89:33 pmMCO - RFD
2 stops20h 02mAllegiant Air
Mon 8/118:42 amRFD - MCO
2 stops11h 01mAllegiant Air
Deal found 1/30$466

Find flights from Orlando to Chicago within your budget

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 January 30, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 2/14

2:41 pm-4:49 pm

Nonstop3h 08m

Chicago O'Hare Intl

Sun 2/16

12:48 pm-11:29 pm

1 stop9h 41m

$93

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 3/6

5:32 pm-7:35 pm

Nonstop3h 03m

Chicago Midway

Mon 3/10

6:38 pm-12:38 am

1 stop5h 00m

$93

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 2/27

5:05 am-7:09 am

Nonstop3h 04m

Chicago O'Hare Intl

Thu 3/6

11:55 am-12:38 am

1 stop11h 43m

$94

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 2/14

6:16 pm-11:58 pm

1 stop6h 42m

Chicago O'Hare Intl

Sun 2/16

8:14 am-12:15 pm

Nonstop3h 01m

$98

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 2/27

5:30 am-11:59 am

1 stop7h 29m

Chicago Midway

Sun 3/2

5:05 pm-12:35 am

1 stop6h 30m

$204

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 2/28

6:20 am-2:00 pm

1 stop8h 40m

Chicago O'Hare Intl

Mon 3/3

11:25 am-7:45 pm

2 stops7h 20m

$216

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 2/26

5:45 pm-7:45 pm

Nonstop3h 00m

Chicago Midway

Tue 3/4

10:25 am-2:05 pm

Nonstop2h 40m

$257

OrlandoChicago

MCO - RFD

MCORFD

Orlando

Wed 3/19

8:45 am-10:43 am

2 stops26h 58m

Chicago Greater Rockford

Mon 3/31

11:33 am-8:55 am

2 stops20h 22m

$458

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 2/14

6:16 pm-11:58 pm

1 stop6h 42m

$58

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 2/18

5:20 am-7:56 pm

1 stop15h 36m

$59

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/29

Showing 1-10 of 22 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 January.
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
Justfly.comPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
MytripPrice Accuracy3 starsTrust Score*3 stars
CheapflightsfaresPrice Accuracy1 starTrust 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.

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.

Travel insights for flights from Orlando to Chicago

Get recent, data-driven insights about flights from Orlando to Chicago including ideal travel times, pricing trends, and more.

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 January 24, 2025.

The best time to book flights from Orlando Airport to Chicago is 89 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 $325). 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 January 30, 2025.

It’s typically best to fly out from Orlando Airport to Chicago in the evening. Doing so could potentially save you 81% 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 January 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 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 January 30, 2025.

The most flights from MCO to CHI are scheduled on a Thursday (58 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (38 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 January 30, 2025.
Get a feel of what it's like to fly with Southwest, Delta and JetBlue 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.
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Bob,Jan 2024

TPA - RDU

No tray tables for food or drink not convenient nor comfortable

Southwest
8.1
Very good
4,585 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Bob,Jan 2024

TPA - RDU

No tray tables for food or drink not convenient nor comfortable

Delta
8.0
Very good
8,450 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Bob,Jan 2024

TPA - RDU

No tray tables for food or drink not convenient nor comfortable

JetBlue
7.4
Good
3,153 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Bob,Jan 2024

TPA - RDU

No tray tables for food or drink not convenient nor comfortable

United Airlines
7.4
Good
8,906 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Bob,Jan 2024

TPA - RDU

No tray tables for food or drink not convenient nor comfortable

Allegiant Air
7.3
Good
790 reviews
Southwest
8.1
Very good
4,585 reviews

Food

7.1

Crew

8.7

Entertainment

7.7

Comfort

8.1

Boarding

8.2

Overall

8.1

Reviews

1 / 20

10.0
Excellent

Bob,Jan 2024

TPA - RDU

No tray tables for food or drink not convenient nor comfortable

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 $93, 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 Delta - these airlines can fly you to your destination from $93 and $204, respectively. Users have found that Spirit Airlines is 48% 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 ($58), Frontier ($59), and Southwest ($99).

  • 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 Emirates (100%), SWISS (97%) or Cathay Pacific (94%) 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 $57. While the most popular route (Orlando - Chicago O'Hare Intl) can be booked for $52 on average our data indicates $1,113 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 $325). 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

Browse thousands of different options on Cheapflights for your next trip

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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 January 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$157FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$58Average$151FlexibilityNo cancel feeOn-time65%
United AirlinesCheapest$149Average$323FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$280FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$178Average$398FlexibilityNo cancel feeOn-time63%
DeltaCheapest$227Average$307FlexibilityNo cancel feeOn-timeN/A
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