Cheap flight from Orlando to Chicago from $43
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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 6:00 AM2h 46mNonstopRFD 7:46 AMOrlando - Chicago | Wed, May 14 | Allegiant Air
RFD 5:41 PM2h 30mNonstopSFB 9:11 PMChicago - Orlando | Fri, May 16 | Allegiant Air$77 $23667% OFF67% OFF$236 $77 -
MCO 9:23 PM3h 9mNonstopORD 11:32 PMOrlando - Chicago | Sat, May 10 | Frontier Airlines
ORD 4:15 PM3h 3mNonstopMCO 8:18 PMChicago - Orlando | Sat, May 17 | Frontier Airlines$80 $23666% OFF66% OFF$236 $80 -
MCO 9:25 PM3h 4mNonstopORD 11:29 PMOrlando - Chicago | Sat, May 17 | Spirit Airlines
ORD 7:47 AM2h 39mNonstopMCO 11:26 AMChicago - Orlando | Mon, May 19 | Spirit Airlines$84 $23664% OFF64% OFF$236 $84 -
MCO 9:25 PM3h 4mNonstopORD 11:29 PMOrlando - Chicago | Sat, May 10 | Spirit Airlines
ORD 4:15 PM3h 3mNonstopMCO 8:18 PMChicago - Orlando | Sat, May 17 | Frontier Airlines$8664% OFF$236 $86
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MCO 9:57 PM3h 7mNonstopORD 12:04 AMOrlando - Chicago | Sat, May 24 | Frontier Airlines
ORD 9:17 AM2h 54mNonstopMCO 1:11 PMChicago - Orlando | Sun, May 25 | Frontier Airlines$8863% OFF$236 $88
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MCO 9:23 PM3h 9mNonstopORD 11:32 PMOrlando - Chicago | Fri, May 2 | Frontier Airlines
ORD 4:15 PM3h 3mNonstopMCO 8:18 PMChicago - Orlando | Sat, May 10 | Frontier Airlines$8863% OFF$236 $88
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SFB 12:09 PM2h 43mNonstopRFD 1:52 PMOrlando - Chicago | Fri, May 23 | Allegiant Air
ORD 5:14 PM2h 57mNonstopMCO 9:11 PMChicago - Orlando | Sun, May 25 | Frontier Airlines$8962% OFF$236 $89
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MCO 10:17 PM3h 3mNonstopORD 12:20 AMOrlando - Chicago | Thu, May 22 | Frontier Airlines
ORD 9:17 AM2h 54mNonstopMCO 1:11 PMChicago - Orlando | Sun, May 25 | Frontier Airlines$11551% OFF$236 $115
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MCO 9:23 PM3h 9mNonstopORD 11:32 PMOrlando - Chicago | Sat, May 17 | Frontier Airlines
ORD 4:15 PM3h 3mNonstopMCO 8:18 PMChicago - Orlando | Mon, May 19 | Frontier Airlines$16132% OFF$236 $161
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MCO 10:17 PM3h 3mNonstopORD 12:20 AMOrlando - Chicago | Fri, May 23 | Frontier Airlines
ORD 9:17 AM2h 54mNonstopMCO 1:11 PMChicago - Orlando | Sun, May 25 | Frontier Airlines$18820% OFF$236 $188
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ORL 1:00 PM17h 25m1 stopsCHI Invalid DateOrlando - Chicago | Sun, May 4 | Normal Airline
CHI 3:00 PM6hNonstopORL 4:00 PMChicago - Orlando | Tue, May 6 | Normal AirlineFind More FlightsFind More Flights
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Cheapest nonstop
SFB 8:10 AM2h 44mNonstopRFD 9:54 AMOrlando - Chicago | Wed, Jun 4 | Allegiant Air$43 $14069% OFF69% OFF$140 $43
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MCO 9:57 PM3h 7mNonstopORD 12:04 AMOrlando - Chicago | Sat, May 24 | Frontier Airlines$44 $14069% OFF69% OFF$140 $44
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SFB 6:20 AM2h 46mNonstopRFD 8:06 AMOrlando - Chicago | Sat, May 31 | Allegiant Air$44 $14069% OFF69% OFF$140 $44
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MCO 9:23 PM3h 9mNonstopORD 11:32 PMOrlando - Chicago | Sat, May 10 | Frontier Airlines$4866% OFF$140 $48
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MCO 9:23 PM3h 9mNonstopORD 11:32 PMOrlando - Chicago | Sat, May 17 | Frontier Airlines$5362% OFF$140 $53
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MCO 9:25 PM3h 4mNonstopORD 11:29 PMOrlando - Chicago | Sat, May 17 | Spirit Airlines$5561% OFF$140 $55
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MCO 6:10 AM3h 12mNonstopORD 8:22 AMOrlando - Chicago | Thu, May 22 | Frontier Airlines$8639% OFF$140 $86
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MCO 9:23 PM3h 9mNonstopORD 11:32 PMOrlando - Chicago | Thu, May 15 | Frontier Airlines$8738% OFF$140 $87
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MCO 9:23 PM3h 9mNonstopORD 11:32 PMOrlando - Chicago | Fri, May 16 | Frontier Airlines$8837% OFF$140 $88
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MCO 10:17 PM3h 19mNonstopORD 12:36 AMOrlando - Chicago | Wed, Jun 11 | Frontier Airlines$11220% OFF$140 $112
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ORL 1:00 PM17h 25m1 stopsCHI Invalid DateOrlando - Chicago | Sun, May 4 | 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.
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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 $280. -
How long does it take to fly from Orlando (ORL) to Chicago (CHI) and what is the distance?
It takes around 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 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.
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
Compare Flight Prices
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Look Out for Deals
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Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com
Flight Info | Orlando to Chicago
| Cheapest one-way flight price | $42 |
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| Cheapest round-trip ticket price | $77 |
| 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 |