Chicago

$57+ 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 7/22. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — CHI
Jul 8 — Jul 151
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Cheapflights Tip: The best prices from Orlando to Chicago are usually found in September or August, 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 (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 July 3, 2025.

Round-trip from

$102
(FlightHub)

One-way from

$57
(FlightHub)

Popular in

March

Cheapest in

September

Average price

$173

Good round-trip deal

$82 or less

Good one-way deal

$94 or less
From Orlando (ORL) to Chicago (CHI)
One-way flight from Orlando (ORL) to Chicago (CHI)
Highest demand for flights based on searches. 7% potential increase in price ($13 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Average for round-trip flights in July 2025
Price to beat on a round-trip flight from Orlando (ORL) to Chicago (CHI).
Price to beat on a one-way flight from Orlando (ORL) 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 July 3, 2025.

This FlightHub deal was found by Cheapflights users on 7/2. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/183:49 pmMCO - ORD
Nonstop3h 09mSpirit Airlines
Tue 7/224:36 pmORD - MCO
Nonstop2h 47mSpirit Airlines
Deal found 7/2$102
This Kiwi.com deal was found by Cheapflights users on 7/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/197:00 amMCO - MDW
Nonstop2h 53mFrontier
Sun 9/219:48 amMDW - MCO
Nonstop2h 40mFrontier
Deal found 7/3$102
This Priceline deal was found by Cheapflights users on 7/3. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/258:23 pmMCO - ORD
Nonstop2h 59mMultiple Airlines
Sat 8/306:00 amORD - MCO
1 stop5h 22mMultiple Airlines
Deal found 7/3$103
This Priceline deal was found by Cheapflights users on 7/2. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1911:07 amMCO - ORD
1 stop5h 03mFrontier
Sun 8/247:46 pmORD - MCO
Nonstop3h 06mFrontier
Deal found 7/2$104
This Kiwi.com deal was found by Cheapflights users on 7/2. 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.
Sat 7/126:30 amSFB - RFD
Nonstop2h 42mAllegiant Air
Fri 7/188:04 pmRFD - SFB
Nonstop2h 35mAllegiant Air
Deal found 7/2$105
This Mytrip deal was found by Cheapflights users on 7/1. 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.
Sat 8/307:36 pmMCO - RFD
2 stops19h 40mMultiple Airlines
Fri 9/510:37 amRFD - MCO
1 stop11h 25mMultiple Airlines
Deal found 7/1$234

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 July 3, 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

MCO - ORD

MCOORD

Orlando

Fri 7/18

3:49 pm-5:58 pm

Nonstop3h 09m

Chicago O'Hare Intl

Tue 7/22

4:36 pm-8:23 pm

Nonstop2h 47m

$102

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 9/19

7:00 am-8:53 am

Nonstop2h 53m

Chicago Midway

Sun 9/21

9:48 am-1:28 pm

Nonstop2h 40m

$102

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Mon 8/25

8:23 pm-10:22 pm

Nonstop2h 59m

Chicago O'Hare Intl

Sat 8/30

6:00 am-12:22 pm

1 stop5h 22m

$103

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 8/19

11:07 am-3:10 pm

1 stop5h 03m

Chicago O'Hare Intl

Sun 8/24

7:46 pm-11:52 pm

Nonstop3h 06m

$104

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Sat 7/12

6:30 am-8:12 am

Nonstop2h 42m

Chicago Greater Rockford

Fri 7/18

8:04 pm-11:39 pm

Nonstop2h 35m

$105

OrlandoChicago

MCO - RFD

MCORFD

Orlando

Sat 8/30

7:36 pm-2:16 pm

2 stops19h 40m

Chicago Greater Rockford

Fri 9/5

10:37 am-11:02 pm

1 stop11h 25m

$234

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Wed 8/6

9:15 am-10:57 am

Nonstop2h 42m

$57

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 7/22

9:59 pm-7:04 am

1 stop10h 05m

$57

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 8/21

12:12 pm-5:05 pm

1 stop5h 53m

$57

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Fri 9/5

1:20 pm-10:43 pm

1 stop10h 23m

$58

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 16 results
1
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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 June 27, 2025.

To ensure you get the cheapest price possible for a flight from Orlando to Chicago, you should look to book at least 89 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 July 3, 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 70% 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 June 29, 2025.

Travelers seeking maximum savings on their Orlando to Chicago flight should consider departing on Friday 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 July 3, 2025.

The most flights from ORL to CHI are scheduled on a Thursday (74 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (23 on average).

How much does it cost to fly round-trip from Orlando to Chicago?

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 July 3, 2025.
Read through reviews of airlines operating flights from Orlando to Chicago, such as Southwest, Delta, and Allegiant Air. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Overall

8.0

Comfort

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.

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Overall

8.0

Comfort

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.
8.0
Very good

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Overall

8.0

Comfort

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.

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Overall

8.0

Comfort

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.

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Overall

8.0

Comfort

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.

Boarding

8.2

Entertainment

7.6

Crew

8.6

Food

7.0

Overall

8.0

Comfort

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 to Chicago round-trip?

    Spirit Airlines, at $102, was found to be the cheapest airline from Orlando to Chicago.Alternate airlines to your destination round-trip include Frontier and Allegiant Air. Spirit Airlines is 45% 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 $57. Users have also found prices from $57 and $58 on Frontier and Allegiant Air, respectively.

  • What are the most popular routes 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: Brussels Airlines (95%), Austrian Airlines (94%), SWISS( 89%).

  • What are the cheapest flights from Orlando to Chicago?

    Looking at all options, your cheapest flight can be booked for $63. While the most popular route (Orlando - Chicago O'Hare Intl) can be booked for $86 on average our data indicates $2,335 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 Orlando?

Book flights to Orlando if you plan to visit one of these locations
Merrillville
Lansing
Benton Harbor
Porter
Hammond
Valparaiso
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.

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 July 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$69Average$165FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$72Average$160FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$90Average$164FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$156Average$332FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$159Average$283FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$173Average$336FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$376FlexibilityNo cancel feeOn-timeN/A

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