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$59+ 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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — CHI
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Orlando to Chicago are usually found in September or August, booked 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 June 12, 2025.

Round-trip from

$106
(Cheapflightsfares)

One-way from

$59
(Booking.com)

Popular in

March

Cheapest in

September

Average price

$221

Good round-trip deal

$104 or less

Good one-way deal

$74 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. 7% potential increase in price ($13 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 June 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 June 12, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 6/9. 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 6/244:38 pmMCO - ORD
Nonstop3h 06mSpirit Airlines
Tue 7/87:49 pmORD - MCO
Nonstop2h 48mSpirit Airlines
Deal found 6/9$106
This Kiwi.com deal was found by Cheapflights users on 6/10. 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.
Wed 7/98:30 amSFB - RFD
Nonstop2h 42mAllegiant Air
Mon 7/148:04 pmRFD - SFB
Nonstop2h 35mAllegiant Air
Deal found 6/10$115
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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.
Sat 8/308:00 amMCO - MDW
Nonstop2h 54mFrontier
Fri 9/58:34 amMDW - MCO
Nonstop2h 41mFrontier
Deal found 6/11$126
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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.
Sat 7/196:05 amMCO - ORD
Nonstop3h 02mFrontier
Tue 7/2211:28 amORD - MCO
Nonstop2h 56mFrontier
Deal found 6/11$127
This Cheapflightsfares deal was found by Cheapflights users on 6/11. 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.
Thu 7/35:01 amMCO - ORD
Nonstop3h 08mMultiple Airlines
Tue 7/87:49 pmORD - MCO
Nonstop2h 48mMultiple Airlines
Deal found 6/11$140
This Southwest deal was found by Cheapflights users on 6/11. 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 8/157:35 amMCO - MDW
Nonstop2h 45mSouthwest
Tue 8/197:55 pmMDW - MCO
Nonstop2h 35mSouthwest
Deal found 6/11$158
This Delta deal was found by Cheapflights users on 6/11. 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.
Wed 7/236:15 amMCO - ORD
1 stop5h 01mDelta
Wed 8/61:35 pmORD - MCO
1 stop5h 16mDelta
Deal found 6/11$197
This Mytrip deal was found by Cheapflights users on 6/10. 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 7/258:27 amMCO - MDW
1 stop6h 37mAllegiant Air
Fri 8/11:11 pmMDW - MCO
1 stop24h 08mAllegiant Air
Deal found 6/10$206
This American Airlines deal was found by Cheapflights users on 6/11. 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.
Fri 10/106:00 amMCO - ORD
Nonstop3h 01mAmerican Airlines
Sat 10/117:00 amORD - MCO
1 stop5h 46mAmerican Airlines
Deal found 6/11$230
This Mytrip deal was found by Cheapflights users on 6/11. 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 7/211:45 amMCO - RFD
1 stop21h 46mMultiple Airlines
Sun 7/69:21 amRFD - MCO
1 stop23h 46mMultiple Airlines
Deal found 6/11$244
This Delta deal was found by Cheapflights users on 6/10. 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 7/196:15 amMCO - MDW
1 stop7h 14mDelta
Tue 7/229:25 amMDW - MCO
1 stop6h 21mDelta
Deal found 6/10$257
This Mytrip deal was found by Cheapflights users on 6/11. 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 8/215:30 amMCO - MDW
2 stops28h 12mMultiple Airlines
Sun 8/2411:03 amMDW - MCO
2 stops28h 04mMultiple Airlines
Deal found 6/11$296

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 June 12, 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

Tue 6/24

4:38 pm-6:44 pm

Nonstop3h 06m

Chicago O'Hare Intl

Tue 7/8

7:49 pm-11:37 pm

Nonstop2h 48m

$106

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Wed 7/9

8:30 am-10:12 am

Nonstop2h 42m

Chicago Greater Rockford

Mon 7/14

8:04 pm-11:39 pm

Nonstop2h 35m

$115

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 8/30

8:00 am-9:54 am

Nonstop2h 54m

Chicago Midway

Fri 9/5

8:34 am-12:15 pm

Nonstop2h 41m

$126

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Sat 7/19

6:05 am-8:07 am

Nonstop3h 02m

Chicago O'Hare Intl

Tue 7/22

11:28 am-3:24 pm

Nonstop2h 56m

$127

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 7/3

5:01 am-7:09 am

Nonstop3h 08m

Chicago O'Hare Intl

Tue 7/8

7:49 pm-11:37 pm

Nonstop2h 48m

$140

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 8/15

7:35 am-9:20 am

Nonstop2h 45m

Chicago Midway

Tue 8/19

7:55 pm-11:30 pm

Nonstop2h 35m

$158

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 7/23

5:45 pm-12:09 am

1 stop7h 24m

Chicago O'Hare Intl

Wed 8/20

5:45 am-10:48 am

1 stop4h 03m

$197

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Fri 7/25

8:27 am-2:04 pm

1 stop6h 37m

Chicago Midway

Fri 8/1

1:11 pm-2:19 pm

1 stop24h 08m

$206

OrlandoChicago

MCO - RFD

MCORFD

Orlando

Wed 7/2

11:45 am-8:31 am

1 stop21h 46m

Chicago Greater Rockford

Sun 7/6

9:21 am-10:07 am

1 stop23h 46m

$244

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Sat 7/19

6:15 am-12:29 pm

1 stop7h 14m

Chicago Midway

Tue 7/22

9:25 am-4:46 pm

1 stop6h 21m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 27 results
1
2
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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 9, 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 June 12, 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 71% 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 8, 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 June 12, 2025.

The most flights from ORL to CHI are scheduled on a Thursday (75 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (35 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 June 12, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and United Airlines from Orlando to Chicago to help guide your decision. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

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
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

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
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

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
7.3
Good
725 reviews
Southwest
8.0
Very good
4,287 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

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
4,287 reviews

Overall

8.0

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Boarding

8.2

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 $106, was found to be the cheapest airline from Orlando to Chicago.Alternate airlines to your destination round-trip include Allegiant Air and Frontier. Spirit Airlines is 43% 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 Allegiant Air. According to our data, you can fly for as low as $59. Users have also found prices from $62 and $79 on Spirit Airlines and Southwest, 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: ANA (91%), SWISS (89%), Japan Airlines( 87%).

  • What are the cheapest flights from Orlando 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 $85 on average our data indicates $1,437 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.
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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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$66Average$165FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$72Average$163FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$100Average$171FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$157Average$329FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$285FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$181Average$338FlexibilityNo cancel feeOn-time63%
DeltaCheapest$196Average$376FlexibilityNo cancel feeOn-timeN/A

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