Cheap Flights from Orlando to Chicago
We've found these cheap flights for you. You can book one-way or round-trip flight tickets.
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Flights from Orlando to Chicago
Cheapest airlines flights from Orlando to Chicago
Compare prices, find the option that best suits your travel needs, and enjoy a comfortable journey with a trusted airline.
Find cheap flights from Orlando to Chicago
We've found these cheap flights for you. You can book one-way or round-trip flight tickets.
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Round-trip
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One way
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Cheapest nonstop
SFB 08:302h 42mNonstopRFD 10:12Orlando - Chicago | Wed, Jul 9 | Allegiant Air
RFD 20:042h 35mNonstopSFB 23:39Chicago - Orlando | Fri, Jul 11 | Allegiant AirUS$86 US$43580% OFF80% OFFUS$435 US$86 -
MCO 21:573h 13mNonstopORD 00:10Orlando - Chicago | Thu, Jun 5 | Frontier Airlines
ORD 16:352h 45mNonstopMCO 20:20Chicago - Orlando | Sat, Jun 7 | Spirit AirlinesUS$161 US$43563% OFF63% OFFUS$435 US$161 -
MCO 21:253h 4mNonstopORD 23:29Orlando - Chicago | Thu, Jun 5 | Spirit Airlines
ORD 16:352h 45mNonstopMCO 20:20Chicago - Orlando | Sat, Jun 7 | Spirit AirlinesUS$165 US$43562% OFF62% OFFUS$435 US$165 -
MCO 21:253h 4mNonstopORD 23:29Orlando - Chicago | Fri, May 30 | Spirit Airlines
ORD 16:352h 45mNonstopMCO 20:20Chicago - Orlando | Sat, May 31 | Spirit AirlinesUS$22748% OFFUS$435 US$227
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MCO 22:173h 3mNonstopORD 00:20Orlando - Chicago | Fri, May 30 | Frontier Airlines
ORD 16:352h 45mNonstopMCO 20:20Chicago - Orlando | Sat, May 31 | Spirit AirlinesUS$23746% OFFUS$435 US$237
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MCO 21:253h 4mNonstopORD 23:29Orlando - Chicago | Sat, May 31 | Spirit Airlines
ORD 17:143h 1mNonstopMCO 21:15Chicago - Orlando | Mon, Jun 2 | Frontier AirlinesUS$23845% OFFUS$435 US$238
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MCO 21:573h 7mNonstopORD 00:04Orlando - Chicago | Sat, May 31 | Frontier Airlines
ORD 17:143h 1mNonstopMCO 21:15Chicago - Orlando | Mon, Jun 2 | Frontier AirlinesUS$23945% OFFUS$435 US$239
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MCO 21:253h 4mNonstopORD 23:29Orlando - Chicago | Thu, May 29 | Spirit Airlines
MDW 21:122h 41mNonstopMCO 00:53Chicago - Orlando | Sun, Jun 1 | Frontier AirlinesUS$24344% OFFUS$435 US$243
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MCO 18:202h 57mNonstopMDW 20:17Orlando - Chicago | Thu, May 29 | Frontier Airlines
MDW 21:122h 41mNonstopMCO 00:53Chicago - Orlando | Sun, Jun 1 | Frontier AirlinesUS$24843% OFFUS$435 US$248
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MCO 22:173h 3mNonstopORD 00:20Orlando - Chicago | Fri, May 23 | Frontier Airlines
ORD 09:172h 54mNonstopMCO 13:11Chicago - Orlando | Sun, May 25 | Frontier AirlinesUS$31827% OFFUS$435 US$318
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ORL 13:0017h 25m1 stopsCHI Invalid DateOrlando - Chicago | Sun, May 25 | Normal Airline
CHI 15:006hNonstopORL 16:00Chicago - Orlando | Tue, May 27 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstop
MCO 21:253h 4mNonstopORD 23:29Orlando - Chicago | Sat, Jun 7 | Spirit AirlinesUS$41 US$16876% OFF76% OFFUS$168 US$41
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MCO 22:173h 19mNonstopORD 00:36Orlando - Chicago | Wed, Jun 11 | Frontier AirlinesUS$50 US$16870% OFF70% OFFUS$168 US$50
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MCO 05:013h 8mNonstopORD 07:09Orlando - Chicago | Sun, Jun 15 | Frontier AirlinesUS$70 US$16859% OFF59% OFFUS$168 US$70
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MCO 22:173h 19mNonstopORD 00:36Orlando - Chicago | Wed, Jun 4 | Frontier AirlinesUS$8053% OFFUS$168 US$80
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MCO 17:553h 8mNonstopORD 20:03Orlando - Chicago | Wed, Jun 4 | Spirit AirlinesUS$8251% OFFUS$168 US$82
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MCO 22:173h 3mNonstopORD 00:20Orlando - Chicago | Wed, May 28 | Frontier AirlinesUS$10041% OFFUS$168 US$100
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MCO 22:173h 3mNonstopORD 00:20Orlando - Chicago | Thu, May 29 | Frontier AirlinesUS$11035% OFFUS$168 US$110
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MCO 21:253h 4mNonstopORD 23:29Orlando - Chicago | Sat, May 31 | Spirit AirlinesUS$11433% OFFUS$168 US$114
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MCO 21:573h 7mNonstopORD 00:04Orlando - Chicago | Sat, May 31 | Frontier AirlinesUS$11532% OFFUS$168 US$115
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MCO 22:173h 19mNonstopORD 00:36Orlando - Chicago | Mon, Jun 2 | Frontier AirlinesUS$12327% OFFUS$168 US$123
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ORL 13:0017h 25m1 stopsCHI Invalid DateOrlando - Chicago | Sun, May 25 | Normal AirlineFind More FlightsFind More Flights
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Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.
Orlando to Chicago Flight Information
| Cheapest one-way flight price | $40 |
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| Cheapest round-trip ticket price | $85 |
| Off-season for travel | April |
| Peak season for travel | February |
| Flight distance | 1,588.53 km |
| Average flight time | 3 hours 28 minutes |
| Popular airline | United Airlines |
When is the cheapest time to book flights from Orlando to Chicago?
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Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.
Frequently Asked Questions
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When are flight tickets from Orlando (ORL) to Chicago (CHI) the cheapest?
Airlines adjust prices for flights from Orlando to Chicago based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays. -
How much do flights from Orlando (ORL) to Chicago (CHI) cost?
According to Trip.com's data, the lowest price is around $284. -
How long does it take to fly from Orlando (ORL) to Chicago (CHI) and what is the distance?
It takes around 3 hours 28 minutes to fly from Orlando (ORL) to Chicago (CHI). -
What are the most popular airlines that fly from Orlando (ORL) to Chicago (CHI)?
Airlines with flights from Orlando (ORL) to Chicago (CHI): Spirit Airlines, Iberia, Alaska Airlines, United Airlines, Allegiant Air, Azul Airlines, Frontier Airlines, Southwest Airlines and Qatar Airways.
How to find a cheap flight from Orlando to Chicago
Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Orlando to Chicago. Book your flights at the right time and save more.
Being flexible with your dates to get the cheapest Orlando to Chicago ticket.
Tap "Date" on flight search bar to scan through the calender for Orlando to Chicago airfare over next 6 months in 2025. If you would like to fly in next 3 months, it seems the cheapest date is on Sat, Jun 7 at US$41 for one-way flights.
Compare cheap Orlando to Chicago flight deals from over hundreds of airlines.
Our extensive search allows you to compare prices from over 500 airlines to choose the cheapest flight tickets from Orlando to Chicago. The cheapest airline operating is Spirit Airlines.
Set up a Price Alert
By setting up a Price Alert for your Orlando to Chicago route, you can easily track the price of your airline tickets from Orlando to Chicago without manually checking every day.
Don't miss cheap Orlando to Chicago flight deals and promo codes.
You can always get the latest deals through Trip.com Deals and Promo Codes for cheap flights for cheap flights. If registering a free membership, you can receive more deals for your flights.
Book early or wait unitl the last minute.
It's always better to book early. Flight tickets tend to be the cheapest when they are first released, normally about a year before the departure date. So, check online as soon as the flights you want become available. If you miss the cheapest time, you can still find lower-priced tickets as the flight date approaches.
Search for flights on the go.
To get the best flight booking experience on the go, download Trip.com free app and search for cheap flight tickets from Orlando to Chicago to get exclusive deals for you.
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