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$62+ 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 8/13. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — CHI
Jul 23 — Jul 301
Wed 7/23
Wed 7/30
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 July 18, 2025.

Round-trip from

$110
(Kiwi.com)

One-way from

$62
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$179

Good round-trip deal

$96 or less

Good one-way deal

$52 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. 4% potential increase in price ($7 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 July 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 July 18, 2025.

This Kiwi.com deal was found by Cheapflights users on 7/16. 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.
Mon 8/45:40 pmSFB - RFD
Nonstop2h 39mAllegiant Air
Sat 8/99:02 amRFD - SFB
Nonstop2h 37mAllegiant Air
Deal found 7/16$110
This Kiwi.com deal was found by Cheapflights users on 7/17. 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.
Thu 8/78:00 amMCO - ORD
Nonstop3h 06mSpirit Airlines
Fri 8/84:36 pmORD - MCO
Nonstop2h 47mSpirit Airlines
Deal found 7/17$113
This Kiwi.com deal was found by Cheapflights users on 7/17. 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 8/166:05 amMCO - ORD
Nonstop3h 02mMultiple Airlines
Sun 8/176:56 amORD - MCO
Nonstop2h 38mMultiple Airlines
Deal found 7/17$120
This FlightHub deal was found by Cheapflights users on 7/17. 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.
Sat 8/166:23 pmMCO - MDW
Nonstop2h 59mFrontier
Sat 8/2310:51 amMDW - MCO
Nonstop2h 43mFrontier
Deal found 7/17$126
This Cheapflightsfares deal was found by Cheapflights users on 7/15. 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.
Tue 8/58:00 amMCO - ORD
Nonstop3h 14mFrontier
Sun 8/104:53 pmORD - MCO
Nonstop3h 02mFrontier
Deal found 7/15$128
This United Airlines deal was found by Cheapflights users on 7/17. 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.
Tue 12/236:00 amMCO - ORD
Nonstop2h 59mUnited Airlines
Tue 1/62:20 pmORD - MCO
Nonstop2h 40mUnited Airlines
Deal found 7/17$157
This Southwest deal was found by Cheapflights users on 7/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/76:20 amMCO - MDW
Nonstop2h 45mSouthwest
Mon 8/111:00 pmMDW - MCO
Nonstop2h 40mSouthwest
Deal found 7/15$157
This Mytrip deal was found by Cheapflights users on 7/17. 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 9/126:00 amMCO - RFD
2 stops9h 25mMultiple Airlines
Mon 9/1510:37 amRFD - MCO
1 stop11h 25mMultiple Airlines
Deal found 7/17$219

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 18, 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

Mon 8/4

5:40 pm-7:19 pm

Nonstop2h 39m

Chicago Greater Rockford

Sat 8/9

9:02 am-12:39 pm

Nonstop2h 37m

$110

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 8/7

8:00 am-10:06 am

Nonstop3h 06m

Chicago O'Hare Intl

Fri 8/8

4:36 pm-8:23 pm

Nonstop2h 47m

$113

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 8/16

6:05 am-8:07 am

Nonstop3h 02m

Chicago O'Hare Intl

Sun 8/17

6:56 am-10:34 am

Nonstop2h 38m

$120

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 8/16

6:23 pm-8:22 pm

Nonstop2h 59m

Chicago Midway

Sat 8/23

10:51 am-2:34 pm

Nonstop2h 43m

$126

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 8/5

8:00 am-10:14 am

Nonstop3h 14m

Chicago O'Hare Intl

Sun 8/10

4:53 pm-8:55 pm

Nonstop3h 02m

$128

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 12/23

6:00 am-7:59 am

Nonstop2h 59m

Chicago O'Hare Intl

Tue 1/6

2:20 pm-6:00 pm

Nonstop2h 40m

$157

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Thu 8/7

6:20 am-8:05 am

Nonstop2h 45m

Chicago Midway

Mon 8/11

1:00 pm-4:40 pm

Nonstop2h 40m

$157

OrlandoChicago

MCO - RFD

MCORFD

Orlando

Fri 9/12

6:00 am-2:25 pm

2 stops9h 25m

Chicago Greater Rockford

Mon 9/15

10:37 am-11:02 pm

1 stop11h 25m

$219

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 8/13

10:16 am-7:42 pm

1 stop10h 26m

$62

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Fri 8/29

9:00 am-10:46 am

Nonstop2h 46m

$64

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/17

Showing 1-10 of 23 results
1
2
3

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 July 11, 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 July 18, 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 67% 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 July 13, 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. Wednesday 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 18, 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 (33 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 18, 2025.
Read through reviews of airlines operating flights from Orlando to Chicago, such as Southwest, Delta, and United Airlines. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,239 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Boarding

8.1

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
4,239 reviews
Southwest
8.0
Very good
4,239 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Boarding

8.1

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
7,959 reviews
Southwest
8.0
Very good
4,239 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Boarding

8.1

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.
United Airlines
7.4
Good
8,864 reviews
Southwest
8.0
Very good
4,239 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Boarding

8.1

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
702 reviews
Southwest
8.0
Very good
4,239 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Boarding

8.1

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
8,038 reviews
Southwest
8.0
Very good
4,239 reviews

Food

7.0

Crew

8.6

Comfort

8.0

Entertainment

7.6

Boarding

8.1

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 to Chicago round-trip?

    Allegiant Air, at $110, was found to be the cheapest airline from Orlando to Chicago.Alternate airlines to your destination round-trip include Spirit Airlines and Frontier. Allegiant Air is 41% 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 $62. Users have also found prices from $64 and $68 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 - 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: Brussels Airlines (93%), Austrian Airlines (93%), Cathay Pacific( 88%).

  • What are the cheapest flights from Orlando to Chicago?

    Looking at all options, your cheapest flight can be booked for $61. While the most popular route (Orlando - Chicago O'Hare Intl) can be booked for $95 on average our data indicates $2,338 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
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.
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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 July 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$72Average$170FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$72Average$158FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$90Average$132FlexibilityNo cancel feeOn-time88%
DeltaCheapest$114Average$346FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$157Average$333FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$284FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$168Average$327FlexibilityNo cancel feeOn-time63%

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