Flights from Chicago to Orlando (CHI to ORL)

Discover more affordable routes and cheaper dates from Chicago to Orlando (CHI to ORL) within a date range.

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  • USD 127
    Frontier Airlines
    8:03pm - 6:14am
    Fri May 2nd
    9h 11m
    Chicago (MDW) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 Frontier Airlines · F9 2209 Depart at 8:03pm from Chicago (MDW) Fly for 2h 53m Arrive at 9:56pm in Denver (DEN)

    Layover in Denver for 2h 34m

    Sat May 3rd 2025 Frontier Airlines · F9 1734 Depart at 12:30am from Denver (DEN) Fly for 3h 44m Arrive at 6:14am in Orlando (MCO)

  • USD 133
    Frontier Airlines
    8:03pm - 2:58pm
    Fri May 2nd
    17h 55m
    Chicago (MDW) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 Frontier Airlines · F9 2209 Depart at 8:03pm from Chicago (MDW) Fly for 2h 53m Arrive at 9:56pm in Denver (DEN)

    Layover in Denver for 11h 17m

    Sat May 3rd 2025 Frontier Airlines · F9 3312 Depart at 9:13am from Denver (DEN) Fly for 3h 45m Arrive at 2:58pm in Orlando (MCO)

  • USD 236
    Frontier Airlines
    8:14pm - 7:30am
    Fri May 2nd
    10h 16m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 Frontier Airlines · F9 2145 Depart at 8:14pm from Chicago (ORD) Fly for 4h 16m Arrive at 10:30pm in Las Vegas (LAS)

    Layover in Las Vegas for 1h 21m

    Fri May 2nd 2025 Frontier Airlines · F9 1876 Depart at 11:51pm from Las Vegas (LAS) Fly for 4h 39m Arrive at 7:30am in Orlando (MCO)

  • USD 370
    United Airlines
    9:45pm - 9:14am
    Fri May 2nd
    10h 29m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 1209 Depart at 9:45pm from Chicago (ORD) Fly for 2h 13m Arrive at 12:58am in New York (EWR)

    Layover in New York for 5h 27m

    Sat May 3rd 2025 United Airlines · UA 774 Depart at 6:25am from New York (EWR) Fly for 2h 49m Arrive at 9:14am in Orlando (MCO)

  • USD 370
    United Airlines
    9:45pm - 9:47am
    Fri May 2nd
    11h 2m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 1209 Depart at 9:45pm from Chicago (ORD) Fly for 2h 13m Arrive at 12:58am in New York (EWR)

    Layover in New York for 5h 57m

    Sat May 3rd 2025 United Airlines · UA 1865 Depart at 6:55am from New York (EWR) Fly for 2h 52m Arrive at 9:47am in Orlando (MCO)

  • USD 381
    United Airlines
    9:45pm - 10:47am
    Fri May 2nd
    12h 2m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 1209 Depart at 9:45pm from Chicago (ORD) Fly for 2h 13m Arrive at 12:58am in New York (EWR)

    Layover in New York for 6h 57m

    Sat May 3rd 2025 United Airlines · UA 1493 Depart at 7:55am from New York (EWR) Fly for 2h 52m Arrive at 10:47am in Orlando (MCO)

  • USD 384
    United Airlines
    9:45pm - 12:02pm
    Fri May 2nd
    13h 17m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 1209 Depart at 9:45pm from Chicago (ORD) Fly for 2h 13m Arrive at 12:58am in New York (EWR)

    Layover in New York for 8h 4m

    Sat May 3rd 2025 United Airlines · UA 1344 Depart at 9:02am from New York (EWR) Fly for 3h 0m Arrive at 12:02pm in Orlando (MCO)

  • USD 384
    United Airlines
    9:45pm - 1:30pm
    Fri May 2nd
    14h 45m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 1209 Depart at 9:45pm from Chicago (ORD) Fly for 2h 13m Arrive at 12:58am in New York (EWR)

    Layover in New York for 9h 32m

    Sat May 3rd 2025 United Airlines · UA 1739 Depart at 10:30am from New York (EWR) Fly for 3h 0m Arrive at 1:30pm in Orlando (MCO)

  • USD 384
    United Airlines
    9:45pm - 2:26pm
    Fri May 2nd
    15h 41m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 1209 Depart at 9:45pm from Chicago (ORD) Fly for 2h 13m Arrive at 12:58am in New York (EWR)

    Layover in New York for 10h 32m

    Sat May 3rd 2025 United Airlines · UA 2114 Depart at 11:30am from New York (EWR) Fly for 2h 56m Arrive at 2:26pm in Orlando (MCO)

  • USD 384
    United Airlines
    9:45pm - 3:28pm
    Fri May 2nd
    16h 43m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 1209 Depart at 9:45pm from Chicago (ORD) Fly for 2h 13m Arrive at 12:58am in New York (EWR)

    Layover in New York for 11h 34m

    Sat May 3rd 2025 United Airlines · UA 1409 Depart at 12:32pm from New York (EWR) Fly for 2h 56m Arrive at 3:28pm in Orlando (MCO)

  • USD 384
    United Airlines
    9:45pm - 5:43pm
    Fri May 2nd
    18h 58m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 1209 Depart at 9:45pm from Chicago (ORD) Fly for 2h 13m Arrive at 12:58am in New York (EWR)

    Layover in New York for 13h 49m

    Sat May 3rd 2025 United Airlines · UA 1213 Depart at 2:47pm from New York (EWR) Fly for 2h 56m Arrive at 5:43pm in Orlando (MCO)

  • USD 384
    United Airlines
    9:45pm - 6:28pm
    Fri May 2nd
    19h 43m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 1209 Depart at 9:45pm from Chicago (ORD) Fly for 2h 13m Arrive at 12:58am in New York (EWR)

    Layover in New York for 14h 34m

    Sat May 3rd 2025 United Airlines · UA 2376 Depart at 3:32pm from New York (EWR) Fly for 2h 56m Arrive at 6:28pm in Orlando (MCO)

  • USD 384
    United Airlines
    9:45pm - 7:55pm
    Fri May 2nd
    21h 10m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 1209 Depart at 9:45pm from Chicago (ORD) Fly for 2h 13m Arrive at 12:58am in New York (EWR)

    Layover in New York for 16h 1m

    Sat May 3rd 2025 United Airlines · UA 1358 Depart at 4:59pm from New York (EWR) Fly for 2h 56m Arrive at 7:55pm in Orlando (MCO)

  • USD 384
    United Airlines
    9:45pm - 10:00pm
    Fri May 2nd
    23h 15m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 1209 Depart at 9:45pm from Chicago (ORD) Fly for 2h 13m Arrive at 12:58am in New York (EWR)

    Layover in New York for 18h 2m

    Sat May 3rd 2025 United Airlines · UA 1331 Depart at 7:00pm from New York (EWR) Fly for 3h 0m Arrive at 10:00pm in Orlando (MCO)

  • USD 413
    United Airlines
    8:15pm - 9:47am
    Fri May 2nd
    12h 32m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 2362 Depart at 8:15pm from Chicago (ORD) Fly for 2h 20m Arrive at 11:35pm in New York (EWR)

    Layover in New York for 7h 20m

    Sat May 3rd 2025 United Airlines · UA 1865 Depart at 6:55am from New York (EWR) Fly for 2h 52m Arrive at 9:47am in Orlando (MCO)

  • USD 414
    Hawaiian Airlines
    6:58pm - 3:19pm
    Fri May 2nd
    19h 21m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 Hawaiian Airlines · HA 6199 Depart at 6:58pm from Chicago (ORD) Fly for 4h 59m Arrive at 9:57pm in San Francisco (SFO)

    Layover in San Francisco for 9h 3m

    Sat May 3rd 2025 Hawaiian Airlines · HA 6999 Depart at 7:00am from San Francisco (SFO) Fly for 5h 19m Arrive at 3:19pm in Orlando (MCO)

  • USD 420
    United Airlines
    9:50pm - 10:47am
    Fri May 2nd
    11h 57m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 2665 Depart at 9:50pm from Chicago (ORD) Fly for 3h 1m Arrive at 12:51am in Houston (IAH)

    Layover in Houston for 6h 29m

    Sat May 3rd 2025 United Airlines · UA 2245 Depart at 7:20am from Houston (IAH) Fly for 2h 27m Arrive at 10:47am in Orlando (MCO)

  • USD 423
    United Airlines
    6:00pm - 5:41am
    Fri May 2nd
    10h 41m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 1943 Depart at 6:00pm from Chicago (ORD) Fly for 2h 55m Arrive at 7:55pm in Denver (DEN)

    Layover in Denver for 4h 4m

    Fri May 2nd 2025 United Airlines · UA 519 Depart at 11:59pm from Denver (DEN) Fly for 3h 42m Arrive at 5:41am in Orlando (MCO)

  • USD 423
    Alaska Airlines
    6:58pm - 3:19pm
    Fri May 2nd
    19h 21m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 Alaska Airlines · AS 597 Depart at 6:58pm from Chicago (ORD) Fly for 4h 59m Arrive at 9:57pm in San Francisco (SFO)

    Layover in San Francisco for 9h 3m

    Sat May 3rd 2025 Alaska Airlines · AS 368 Depart at 7:00am from San Francisco (SFO) Fly for 5h 19m Arrive at 3:19pm in Orlando (MCO)

  • USD 428
    United Airlines
    7:55pm - 10:47am
    Fri May 2nd
    13h 52m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 2155 Depart at 7:55pm from Chicago (ORD) Fly for 3h 3m Arrive at 10:58pm in Houston (IAH)

    Layover in Houston for 8h 22m

    Sat May 3rd 2025 United Airlines · UA 2245 Depart at 7:20am from Houston (IAH) Fly for 2h 27m Arrive at 10:47am in Orlando (MCO)

  • USD 428
    United Airlines
    9:50pm - 12:57pm
    Fri May 2nd
    14h 7m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 2665 Depart at 9:50pm from Chicago (ORD) Fly for 3h 1m Arrive at 12:51am in Houston (IAH)

    Layover in Houston for 8h 39m

    Sat May 3rd 2025 United Airlines · UA 413 Depart at 9:30am from Houston (IAH) Fly for 2h 27m Arrive at 12:57pm in Orlando (MCO)

  • USD 428
    United Airlines
    6:33pm - 10:47am
    Fri May 2nd
    15h 14m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 470 Depart at 6:33pm from Chicago (ORD) Fly for 3h 3m Arrive at 9:36pm in Houston (IAH)

    Layover in Houston for 9h 44m

    Sat May 3rd 2025 United Airlines · UA 2245 Depart at 7:20am from Houston (IAH) Fly for 2h 27m Arrive at 10:47am in Orlando (MCO)

  • USD 428
    United Airlines
    7:55pm - 12:57pm
    Fri May 2nd
    16h 2m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 2155 Depart at 7:55pm from Chicago (ORD) Fly for 3h 3m Arrive at 10:58pm in Houston (IAH)

    Layover in Houston for 10h 32m

    Sat May 3rd 2025 United Airlines · UA 413 Depart at 9:30am from Houston (IAH) Fly for 2h 27m Arrive at 12:57pm in Orlando (MCO)

  • USD 428
    United Airlines
    6:33pm - 12:57pm
    Fri May 2nd
    17h 24m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 470 Depart at 6:33pm from Chicago (ORD) Fly for 3h 3m Arrive at 9:36pm in Houston (IAH)

    Layover in Houston for 11h 54m

    Sat May 3rd 2025 United Airlines · UA 413 Depart at 9:30am from Houston (IAH) Fly for 2h 27m Arrive at 12:57pm in Orlando (MCO)

  • USD 434
    United Airlines
    9:50pm - 3:54pm
    Fri May 2nd
    17h 4m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 2665 Depart at 9:50pm from Chicago (ORD) Fly for 3h 1m Arrive at 12:51am in Houston (IAH)

    Layover in Houston for 11h 35m

    Sat May 3rd 2025 United Airlines · UA 2662 Depart at 12:26pm from Houston (IAH) Fly for 2h 28m Arrive at 3:54pm in Orlando (MCO)

  • USD 434
    United Airlines
    9:50pm - 5:48pm
    Fri May 2nd
    18h 58m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 2665 Depart at 9:50pm from Chicago (ORD) Fly for 3h 1m Arrive at 12:51am in Houston (IAH)

    Layover in Houston for 13h 29m

    Sat May 3rd 2025 United Airlines · UA 496 Depart at 2:20pm from Houston (IAH) Fly for 2h 28m Arrive at 5:48pm in Orlando (MCO)

  • USD 434
    United Airlines
    9:50pm - 8:33pm
    Fri May 2nd
    21h 43m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 2665 Depart at 9:50pm from Chicago (ORD) Fly for 3h 1m Arrive at 12:51am in Houston (IAH)

    Layover in Houston for 16h 14m

    Sat May 3rd 2025 United Airlines · UA 1571 Depart at 5:05pm from Houston (IAH) Fly for 2h 28m Arrive at 8:33pm in Orlando (MCO)

  • USD 434
    United Airlines
    9:50pm - 10:00pm
    Fri May 2nd
    23h 10m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 2665 Depart at 9:50pm from Chicago (ORD) Fly for 3h 1m Arrive at 12:51am in Houston (IAH)

    Layover in Houston for 17h 41m

    Sat May 3rd 2025 United Airlines · UA 2451 Depart at 6:32pm from Houston (IAH) Fly for 2h 28m Arrive at 10:00pm in Orlando (MCO)

  • USD 434
    United Airlines
    9:50pm - 11:44pm
    Fri May 2nd
    24h 54m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 2665 Depart at 9:50pm from Chicago (ORD) Fly for 3h 1m Arrive at 12:51am in Houston (IAH)

    Layover in Houston for 19h 25m

    Sat May 3rd 2025 United Airlines · UA 1352 Depart at 8:16pm from Houston (IAH) Fly for 2h 28m Arrive at 11:44pm in Orlando (MCO)

  • USD 486
    United Airlines
    8:15pm - 9:14am
    Fri May 2nd
    11h 59m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 2362 Depart at 8:15pm from Chicago (ORD) Fly for 2h 20m Arrive at 11:35pm in New York (EWR)

    Layover in New York for 6h 50m

    Sat May 3rd 2025 United Airlines · UA 774 Depart at 6:25am from New York (EWR) Fly for 2h 49m Arrive at 9:14am in Orlando (MCO)

  • USD 573
    United Airlines
    7:45pm - 5:41am
    Fri May 2nd
    8h 56m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 2040 Depart at 7:45pm from Chicago (ORD) Fly for 2h 55m Arrive at 9:40pm in Denver (DEN)

    Layover in Denver for 2h 19m

    Fri May 2nd 2025 United Airlines · UA 519 Depart at 11:59pm from Denver (DEN) Fly for 3h 42m Arrive at 5:41am in Orlando (MCO)

  • USD 574
    United Airlines
    9:17pm - 5:41am
    Fri May 2nd
    7h 24m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 United Airlines · UA 767 Depart at 9:17pm from Chicago (ORD) Fly for 2h 55m Arrive at 11:12pm in Denver (DEN)

    Layover in Denver for 0h 47m

    Fri May 2nd 2025 United Airlines · UA 519 Depart at 11:59pm from Denver (DEN) Fly for 3h 42m Arrive at 5:41am in Orlando (MCO)

  • USD 626
    Hawaiian Airlines
    7:19pm - 4:51pm
    Fri May 2nd
    20h 32m
    Chicago (ORD) → Orlando (MCO)
    1 Stop

    Fri May 2nd 2025 Hawaiian Airlines · HA 6298 Depart at 7:19pm from Chicago (ORD) Fly for 4h 41m Arrive at 10:00pm in Seattle (SEA)

    Layover in Seattle for 9h 55m

    Sat May 3rd 2025 Hawaiian Airlines · HA 6779 Depart at 7:55am from Seattle (SEA) Fly for 5h 56m Arrive at 4:51pm in Orlando (MCO)

@sarahbb1
Sarah Belizaire
@sarahbb1

Have flexible travel plans or looking for alternative routes given the chaos? Check out all the connection possibilities via a super helpful site created by @ismaelyws flightlist.io thanks to @andy_travels for the recommendation #travel #flights

@eyupitsjohn
John Ford
@eyupitsjohn

There seem to be lots of sites launching at the moment that promise to find you cheap flights but not many have the professional finish of Flightlist by @ismaelyws #travel #flights

@oamingsonaa
Roaming Sonaa
@roamingsonaa

For people wanting to maximize their trips, Flightlist is my newest travel hack for uncovering the coolest routes at irresistible prices. No stress, no annoying ads — just seamless flight booking with amazing functionality.

@andy_travels
Andy Travels
@andy_travels

@ismaelyws Just tried out Flightlist for the first time. Really nice idea, well made, and just what I need at the moment 👍

@travelwitbender
Travel With Bender
@travelwitbender

Did you spot my recent article about how to score cheap one way flights? ✈️ FlightList is my new secret tool for discovering cheap routes, within a departure date range. Plus you can also search by country/region for departures & destinations. Powerful! 💪

@travel.with.wes
Wesley Mergard
@travel.with.wes

One useful tool I've found for evaluating different departure and return dates is called FlightList.io. You can quickly scan different travel date ranges, carriers and one way flight options to easily determine the cheapest flight combinations for your trip.

Explore Flight Options

FlightList Blog

Flightlist Interviews 7 Travel Experts On Why They Book One Way Flights
Flightlist Interviews 7 Travel Experts On Why They Book One Way Flights
Why I built FlightList & solved my own problem
Why I Built FlightList & Solved My Own Problem

About FlightList

❝Founded by a remote worker and frequent flyer, who discovered that the best deals come from searching with flexible dates across entire countries or regions. Our streamlined platform strips away the clutter found on typical travel sites, offering a clean interface that focuses solely on finding cost-effective flights. Unlike traditional booking sites, FlightList allows users to search by date ranges and broad destinations, unveiling opportunities that rigid parameters often miss. Our filters let travelers tailor searches to their specific needs, whether they're digital nomads seeking their next adventure or budget-conscious explorers maximizing travel funds. We've made finding cheap flights into a quicker and easier experience, empowering users to discover just how far their budget can take them.❞

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