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$49+ Cheap flights from Orlando (ORL) 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 12/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — CHI
oct. 17 — oct. 241
vie. 10/17
vie. 10/24
1 adult, Economy
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Cheapflights Tip: The best prices from Orlando to Chicago are usually found in September or August, booked 87 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 (ORL) 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 septiembre 17, 2025.

Round-trip from

$86
(Cheapflightsfares)

One-way from

$49
(Kiwi.com)

Popular in

March

Cheapest in

September

Average price

$148

Good round-trip deal

$106 or less

Good one-way deal

$79 or less
From Orlando (ORL) to Chicago (CHI)
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One-way flight from Orlando (ORL) to Chicago (CHI)
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Highest demand for flights based on searches. 5% potential increase in price ($10 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Price to beat on a round-trip flight from Orlando (ORL) to Chicago (CHI).
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Price to beat on a one-way flight from Orlando (ORL) 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 septiembre 17, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
mié. 10/83:53 pmMCO - ORD
Nonstop3h 00mSpirit Airlines
mar. 10/146:58 pmORD - MCO
Nonstop2h 52mSpirit Airlines
Deal found 9/15$86
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/114:23 pmMCO - ORD
Nonstop3h 10mFrontier
dom. 10/128:14 amORD - MCO
Nonstop2h 48mFrontier
Deal found 9/14$87
This Kiwi.com deal was found by Cheapflights users on 9/16. 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. 10/35:24 pmMCO - ORD
Nonstop3h 20mFrontier
sáb. 10/117:43 pmORD - MCO
Nonstop2h 54mFrontier
Deal found 9/16$88
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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. 10/37:50 pmMCO - ORD
Nonstop3h 08mSpirit Airlines
dom. 10/56:00 amORD - MCO
Nonstop2h 44mSpirit Airlines
Deal found 9/15$89
This Kiwi.com deal was found by Cheapflights users on 9/15. 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. 9/265:24 pmMCO - ORD
Nonstop3h 20mFrontier
lun. 9/298:49 pmORD - MCO
Nonstop2h 46mFrontier
Deal found 9/15$90
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
lun. 9/297:50 pmMCO - ORD
Nonstop3h 08mSpirit Airlines
vie. 10/35:17 pmORD - MCO
Nonstop2h 49mSpirit Airlines
Deal found 9/15$91
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/114:23 pmMCO - ORD
Nonstop3h 10mMultiple Airlines
mar. 10/146:58 pmORD - MCO
Nonstop2h 52mMultiple Airlines
Deal found 9/14$92
This Cheapflightsfares deal was found by Cheapflights users on 9/15. 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.
mié. 10/83:53 pmMCO - ORD
Nonstop3h 00mSpirit Airlines
dom. 10/126:00 amORD - MCO
Nonstop2h 44mSpirit Airlines
Deal found 9/15$93
This Kiwi.com deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/175:25 amMCO - ORD
Nonstop3h 09mMultiple Airlines
dom. 10/196:00 amORD - MCO
Nonstop2h 44mMultiple Airlines
Deal found 9/14$94
This Kiwi.com deal was found by Cheapflights users on 9/15. 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. 10/35:24 pmMCO - ORD
Nonstop3h 20mMultiple Airlines
sáb. 10/45:17 pmORD - MCO
Nonstop2h 49mMultiple Airlines
Deal found 9/15$95
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
sáb. 10/48:30 amMCO - MDW
Nonstop2h 51mFrontier
dom. 10/510:13 amMDW - MCO
Nonstop2h 42mFrontier
Deal found 9/15$95
This Priceline deal was found by Cheapflights users on 9/15. 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.
vie. 10/105:25 amMCO - ORD
Nonstop3h 09mMultiple Airlines
lun. 10/137:51 pmORD - MCO
Nonstop2h 52mMultiple Airlines
Deal found 9/15$96

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 septiembre 17, 2025.
Use the filters below to find and compare flights from Orlando to Chicago that are best for you.

Fly from

Orlando

Fly to

Chicago

Route

Depart

Return

Price

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

vie. 10/10

12:33 pm-2:18 pm

Nonstop2h 45m

Chicago Greater Rockford

lun. 10/13

7:47 pm-11:17 pm

Nonstop2h 30m

$112

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

jue. 10/16

8:50 am-10:46 am

Nonstop2h 56m

Chicago Midway

jue. 10/23

5:20 pm-12:59 am

1 stop6h 39m

$112

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

vie. 10/17

12:33 pm-2:18 pm

Nonstop2h 45m

Chicago Greater Rockford

lun. 10/20

7:47 pm-11:17 pm

Nonstop2h 30m

$126

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

mié. 10/15

6:15 am-8:00 am

Nonstop2h 45m

Chicago Greater Rockford

vie. 10/17

7:48 pm-11:18 pm

Nonstop2h 30m

$128

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

mié. 10/8

6:15 am-8:00 am

Nonstop2h 45m

Chicago Greater Rockford

vie. 10/10

7:48 pm-11:18 pm

Nonstop2h 30m

$132

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

jue. 10/30

8:56 am-2:33 pm

1 stop6h 37m

Chicago Midway

lun. 11/3

6:30 am-1:54 pm

1 stop6h 24m

$143

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

vie. 10/31

8:56 am-2:33 pm

1 stop6h 37m

Chicago Midway

lun. 11/3

6:30 am-1:54 pm

1 stop6h 24m

$143

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

sáb. 10/11

1:16 pm-3:11 pm

Nonstop2h 55m

Chicago Midway

mié. 10/15

8:05 am-2:03 pm

1 stop4h 58m

$143

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

vie. 10/24

6:35 am-8:20 am

Nonstop2h 45m

Chicago Midway

mar. 10/28

11:40 am-3:10 pm

Nonstop2h 30m

$158

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

vie. 10/17

6:35 am-8:20 am

Nonstop2h 45m

Chicago Midway

dom. 10/19

8:55 pm-12:30 am

Nonstop2h 35m

$159

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/17

Showing 1-10 of 60 results
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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 to Chicago

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

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

To ensure you get the cheapest price possible for a flight from Orlando to Chicago, you should look to book at least 86 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.

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

Currently, August is the cheapest month in which you can book a flight from Orlando to Chicago (average of $245). Flying from Orlando 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 ORL 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 septiembre 17, 2025.

One of the essential ways to save on airfare from Orlando to Chicago is to remain as flexible as possible. Flights that are at noon tend to be the most expensive. A flight in the evening could potentially save you up to 59% on airfare.

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

Use this chart to determine the cheapest time to fly round-trip from Orlando to Chicago. Price data was last updated on September 14, 2025.

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

Weekly flight availability from Orlando 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 septiembre 17, 2025.

The most flights from ORL to CHI are scheduled on a Monday (76 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (38 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 septiembre 17, 2025.
Read through reviews of airlines operating flights from Orlando to Chicago, such as Southwest, United Airlines, and American Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

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
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

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.
United Airlines
7.4
Good
8,926 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

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
4,242 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

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
8,023 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

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.
Frontier
5.8
Fair
3,173 reviews
Southwest
8.0
Very good
4,242 reviews

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

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

Related info for your journey

Find useful and relevant information for your journey from Orlando to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Orlando to Chicago?

    Departing from Orlando to Chicago will take you 2h 45m. Orlando and Chicago are separated by a distance of 1025 mi. Generally, flights for this route are nonstop.

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

    Frontier, at $72, was found to be the cheapest airline from Orlando to Chicago.Alternate airlines to your destination round-trip include Spirit Airlines and Allegiant Air. Frontier is 62% cheaper than the average price of flights available within the next 90 days to this destination.

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

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $50. Users have also found prices from $62 and $70 on Allegiant Air and Frontier, respectively.

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

    Most travelers choose Orlando - Chicago O'Hare Intl, Orlando - Chicago Midway or Orlando Sanford Intl - Chicago Greater Rockford when deciding on the best route from Orlando to Chicago.

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

    Before booking your flight to Chicago from Orlando, check out the most reliable airlines to get you to your destination on time: ITA Airways (100%), United Airlines (81%), ANA( 79%).

  • What are the cheapest flights from Orlando to Chicago?

    Looking at all options, your cheapest flight can be booked for $54. While the most popular route (Orlando - Chicago O'Hare Intl) can be booked for $76 on average, our data indicates $1,117 when flying from Orlando 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 to Chicago?

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

See more FAQs

Traveling to a place near Chicago?

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

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Alternative routes for Orlando to Chicago

See prices for flight routes from nearby airports that may be better suited for you.
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Top 7 airlines flying from Orlando to Chicago

Discover the top 7 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 septiembre 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$170FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$73Average$140FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$90Average$142FlexibilityNo cancel feeOn-time88%
DeltaCheapest$114Average$332FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$158Average$346FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$277FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$159Average$298FlexibilityNo cancel feeOn-time63%

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