Cheap flight from Orlando to Chicago from AED 158
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Flights from Orlando to Chicago
Cheap flight deals 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 06:002h 46mNonstopRFD 07:46Orlando - Chicago | Wed, May 14 | Allegiant Air
RFD 17:412h 30mNonstopSFB 21:11Chicago - Orlando | Fri, May 16 | Allegiant AirAED 283 AED 85367% OFF67% OFFAED 853 AED 283 -
MCO 21:573h 7mNonstopORD 00:04Orlando - Chicago | Sat, May 24 | Frontier Airlines
ORD 09:172h 54mNonstopMCO 13:11Chicago - Orlando | Sun, May 25 | Frontier AirlinesAED 323 AED 85362% OFF62% OFFAED 853 AED 323 -
SFB 12:092h 43mNonstopRFD 13:52Orlando - Chicago | Fri, May 23 | Allegiant Air
ORD 17:142h 57mNonstopMCO 21:11Chicago - Orlando | Sun, May 25 | Frontier AirlinesAED 326 AED 85362% OFF62% OFFAED 853 AED 326
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MCO 21:233h 9mNonstopORD 23:32Orlando - Chicago | Sat, May 10 | Frontier Airlines
ORD 16:153h 3mNonstopMCO 20:18Chicago - Orlando | Sat, May 17 | Frontier AirlinesAED 33461% OFFAED 853 AED 334
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MCO 21:253h 4mNonstopORD 23:29Orlando - Chicago | Wed, May 7 | Spirit Airlines
ORD 07:472h 39mNonstopMCO 11:26Chicago - Orlando | Tue, May 13 | Spirit AirlinesAED 33661% OFFAED 853 AED 336 -
MCO 22:173h 3mNonstopORD 00:20Orlando - Chicago | Thu, May 22 | Frontier Airlines
ORD 09:172h 54mNonstopMCO 13:11Chicago - Orlando | Sun, May 25 | Frontier AirlinesAED 58132% OFFAED 853 AED 581
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MCO 21:253h 4mNonstopORD 23:29Orlando - Chicago | Sat, May 10 | Spirit Airlines
ORD 16:153h 3mNonstopMCO 20:18Chicago - Orlando | Sat, May 17 | Frontier AirlinesAED 60130% OFFAED 853 AED 601
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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 AirlinesAED 69219% OFFAED 853 AED 692
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MCO 21:253h 4mNonstopORD 23:29Orlando - Chicago | Sat, May 17 | Spirit Airlines
ORD 07:472h 39mNonstopMCO 11:26Chicago - Orlando | Mon, May 19 | Spirit AirlinesAED 70717% OFFAED 853 AED 707
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MCO 21:233h 9mNonstopORD 23:32Orlando - Chicago | Sat, May 17 | Frontier Airlines
ORD 16:153h 3mNonstopMCO 20:18Chicago - Orlando | Mon, May 19 | Frontier AirlinesAED 70817% OFFAED 853 AED 708
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ORL 13:0017h 25m1 stopsCHI Invalid DateOrlando - Chicago | Mon, May 5 | Normal Airline
CHI 15:006hNonstopORL 16:00Chicago - Orlando | Wed, May 7 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstop
SFB 08:102h 44mNonstopRFD 09:54Orlando - Chicago | Wed, Jun 4 | Allegiant AirAED 158 AED 50369% OFF69% OFFAED 503 AED 158
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SFB 06:202h 44mNonstopRFD 08:04Orlando - Chicago | Sat, Jun 7 | Allegiant AirAED 161 AED 50368% OFF68% OFFAED 503 AED 161
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SFB 06:202h 46mNonstopRFD 08:06Orlando - Chicago | Sat, May 31 | Allegiant AirAED 162 AED 50368% OFF68% OFFAED 503 AED 162
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MCO 21:233h 9mNonstopORD 23:32Orlando - Chicago | Sat, May 10 | Frontier AirlinesAED 17665% OFFAED 503 AED 176
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MCO 21:573h 7mNonstopORD 00:04Orlando - Chicago | Sat, May 24 | Frontier AirlinesAED 17665% OFFAED 503 AED 176
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MCO 21:233h 9mNonstopORD 23:32Orlando - Chicago | Fri, May 16 | Frontier AirlinesAED 28843% OFFAED 503 AED 288
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MCO 06:103h 12mNonstopORD 08:22Orlando - Chicago | Thu, May 22 | Frontier AirlinesAED 31438% OFFAED 503 AED 314
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MCO 21:233h 9mNonstopORD 23:32Orlando - Chicago | Thu, May 15 | Frontier AirlinesAED 32435% OFFAED 503 AED 324
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MCO 22:173h 19mNonstopORD 00:36Orlando - Chicago | Wed, Jun 11 | Frontier AirlinesAED 41218% OFFAED 503 AED 412
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MCO 21:233h 9mNonstopORD 23:32Orlando - Chicago | Sat, May 17 | Frontier AirlinesAED 41717% OFFAED 503 AED 417
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ORL 13:0017h 25m1 stopsCHI Invalid DateOrlando - Chicago | Mon, May 5 | 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.
Flight Info | Orlando to Chicago
| Cheapest one-way flight price | AED 157 |
|---|---|
| Cheapest return ticket price | AED 283 |
| Off-season for travel | March |
| Peak season for travel | June |
| Flight distance | 1,588.53 km |
| Average flight time | 3 hours 41 minutes |
| Popular airline | Jetblue Airways |
When is the cheapest time to fly 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 date and time of your booking. By analyzing data from all airlines, 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 AED 1,031. -
How long does it take to fly from Orlando (ORL) to Chicago (CHI)?
It takes about 3 hours 41 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, American Airlines, Frontier Airlines, Southwest Airlines, Azul Airlines and Qatar Airways. -
How many airports are there in Chicago (CHI)?
There are 3 airport(s) near Chicago (CHI): Midway International Airport, O'Hare International Airport and Chicago Rockford International Airport.
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 Wed, Jun 4 at AED 158 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 Allegiant Air.
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 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. 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 and search for cheap flight tickets from Orlando to Chicago to get exclusive deals for you.
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