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$53+ 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 3/25. Fares are subject to change and may not be available on all flights or dates of travel.
ORL — CHI
Mar 2 — Mar 91
Sun 3/2
Sun 3/9
1 adult, Economy
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Find cheap flights from Orlando to Chicago with Cheapflights

1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”
2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.
3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

The best prices from Orlando to Chicago are usually found in February or April, booked 76 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 February 25, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$81
(Cheapflightsfares)

One-way from

$53
(Mytrip)

Popular in

June

Cheapest in

February

Average price

$138

Good round-trip deal

$149 or less

Good one-way deal

$100 or less
Provider with most accurate pricing for Orlando (ORL)-Chicago (CHI) flight deals.
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Provider most trusted by Cheapflights users for Orlando (ORL)-Chicago (CHI) flights.
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From Orlando (ORL) to Chicago (CHI)
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One-way flight from Orlando (ORL) to Chicago (CHI)
Search Deals
Highest demand for flights based on searches. 5% potential increase in price ($10 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2025
Search Deals
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 February 25, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 2/23. 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 3/184:37 pmMCO - ORD
Nonstop3h 17mMultiple Airlines
Tue 3/259:08 pmORD - MCO
Nonstop2h 51mMultiple Airlines
Deal found 2/23$81
This FlightHub deal was found by Cheapflights users on 2/24. 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.
Tue 3/258:54 amMCO - ORD
Nonstop3h 15mSpirit Airlines
Wed 3/269:08 pmORD - MCO
Nonstop2h 51mSpirit Airlines
Deal found 2/24$84
This CheapOair deal was found by Cheapflights users on 2/23. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/25:34 pmMCO - MDW
Nonstop3h 01mFrontier
Sun 4/610:19 amMDW - MCO
Nonstop2h 50mFrontier
Deal found 2/23$123
This Frontier deal was found by Cheapflights users on 2/24. 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.
Wed 7/169:23 pmMCO - ORD
Nonstop3h 15mFrontier
Sat 7/194:21 pmORD - MCO
Nonstop2h 57mFrontier
Deal found 2/24$138
This Mytrip deal was found by Cheapflights users on 2/24. 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 4/184:02 pmSFB - RFD
Nonstop2h 42mAllegiant Air
Mon 4/216:34 pmRFD - SFB
Nonstop2h 34mAllegiant Air
Deal found 2/24$147
This Delta deal was found by Cheapflights users on 2/25. 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 4/176:05 amMCO - ORD
1 stop7h 34mDelta
Wed 4/2310:30 amORD - MCO
1 stop7h 00mDelta
Deal found 2/25$203
This Southwest deal was found by Cheapflights users on 2/24. 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.
Tue 4/17:30 amMCO - MDW
1 stop5h 30mSouthwest
Tue 4/88:30 amMDW - MCO
1 stop4h 25mSouthwest
Deal found 2/24$204
This Delta deal was found by Cheapflights users on 2/24. 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 3/268:45 amMCO - MDW
1 stop4h 51mDelta
Wed 4/24:59 pmMDW - MCO
1 stop5h 59mDelta
Deal found 2/24$209
This JetBlue deal was found by Cheapflights users on 2/24. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/196:20 amMCO - ORD
1 stop6h 57mJetBlue
Wed 5/281:12 pmORD - MCO
1 stop8h 45mJetBlue
Deal found 2/24$228
This Mytrip deal was found by Cheapflights users on 2/24. 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 4/184:08 pmMCO - RFD
2 stops17h 58mAllegiant Air
Mon 4/218:58 amRFD - MCO
2 stops24h 47mAllegiant Air
Deal found 2/24$478
This Mytrip deal was found by Cheapflights users on 2/25. 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.
Mon 3/107:00 amMCO - RFD
2 stops27h 00mMultiple Airlines
Tue 3/117:02 pmRFD - MCO
3 stops27h 57mMultiple Airlines
Deal found 2/25$570

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 February 25, 2025.

Fly from

Orlando

Fly to

Chicago

Route

Depart

Return

Price

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 3/18

4:37 pm-6:54 pm

Nonstop3h 17m

Chicago O'Hare Intl

Tue 3/25

9:08 pm-12:59 am

Nonstop2h 51m

$81

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Tue 3/25

8:54 am-11:09 am

Nonstop3h 15m

Chicago O'Hare Intl

Wed 3/26

9:08 pm-12:59 am

Nonstop2h 51m

$84

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Wed 3/26

6:40 am-9:05 am

Nonstop3h 25m

Chicago O'Hare Intl

Sun 3/30

9:25 am-1:20 pm

Nonstop2h 55m

$116

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 4/2

5:34 pm-7:35 pm

Nonstop3h 01m

Chicago Midway

Sun 4/6

10:19 am-2:09 pm

Nonstop2h 50m

$123

OrlandoChicago

SFB - RFD

SFBRFD

Orlando Sanford Intl

Fri 4/18

4:02 pm-5:44 pm

Nonstop2h 42m

Chicago Greater Rockford

Mon 4/21

6:34 pm-10:08 pm

Nonstop2h 34m

$147

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Thu 4/17

6:05 am-12:39 pm

1 stop7h 34m

Chicago O'Hare Intl

Wed 4/23

10:30 am-6:30 pm

1 stop7h 00m

$203

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Tue 4/1

7:45 am-12:50 pm

1 stop6h 05m

Chicago Midway

Tue 4/8

8:30 am-1:55 pm

1 stop4h 25m

$204

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 3/26

8:45 am-12:36 pm

1 stop4h 51m

Chicago Midway

Wed 4/2

4:59 pm-11:58 pm

1 stop5h 59m

$209

OrlandoChicago

MCO - ORD

MCOORD

Orlando

Mon 5/19

6:20 am-12:17 pm

1 stop6h 57m

Chicago O'Hare Intl

Wed 5/28

1:12 pm-10:57 pm

1 stop8h 45m

$228

OrlandoChicago

MCO - MDW

MCOMDW

Orlando

Wed 3/19

6:40 pm-5:36 pm

2 stops23h 56m

Chicago Midway

Mon 3/31

8:40 am-7:09 am

3 stops45h 29m

$374

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/23

Showing 1-10 of 29 results
1
2
3

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 February.
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
Kiwi.comPrice Accuracy3 starsTrust Score*2 stars
Trip.comPrice Accuracy1 starTrust Score*3 stars
FlightnetworkPrice Accuracy-Trust Score*3 stars
CheapOairPrice Accuracy1 starTrust Score*3 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-Chicago flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Orlando-Chicago flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Orlando-Chicago flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Orlando-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-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 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 February 14, 2025.

To ensure you get the cheapest price possible for a flight from Orlando to Chicago, you should look to book at least 76 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 $322). 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 February 25, 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 79% 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 February 23, 2025.

Travelers seeking maximum savings on their Orlando 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 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 February 25, 2025.

The most flights from ORL to CHI are scheduled on a Thursday (67 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (47 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 February 25, 2025.
Peruse reviews from past customers who have flown with Southwest, Delta and JetBlue 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
8.1
Very good
4,374 reviews

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.6

Food

7.1

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
8.1
Very good
4,374 reviews
Southwest
8.1
Very good
4,374 reviews

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.6

Food

7.1

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
8,163 reviews
Southwest
8.1
Very good
4,374 reviews

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.6

Food

7.1

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.

JetBlue
7.4
Good
3,051 reviews
Southwest
8.1
Very good
4,374 reviews

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.6

Food

7.1

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
8,734 reviews
Southwest
8.1
Very good
4,374 reviews

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.6

Food

7.1

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
759 reviews
Southwest
8.1
Very good
4,374 reviews

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Entertainment

7.6

Food

7.1

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 $84, 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 53% 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 $53. Users have also found prices from $68 and $69 on Frontier and Allegiant Air, 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: Austrian Airlines (97%), Japan Airlines (95%), Brussels Airlines( 95%).

  • What are the cheapest flights from Orlando to Chicago?

    Looking at all options, your cheapest flight can be booked for $51. While the most popular route (Orlando - Chicago O'Hare Intl) can be booked for $83 on average our data indicates $978 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 $322). 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
New Buffalo
Hammond
Benton Harbor
Porter
Lansing
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 February 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
FrontierCheapest$58Average$149FlexibilityNo cancel feeOn-time62%
Spirit AirlinesCheapest$58Average$153FlexibilityNo cancel feeOn-time65%
Allegiant AirCheapest$112Average$197FlexibilityNo cancel feeOn-time88%
United AirlinesCheapest$151Average$322FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$158Average$283FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$179Average$398FlexibilityNo cancel feeOn-time63%
DeltaCheapest$227Average$334FlexibilityNo cancel feeOn-timeN/A
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