United Airlines Chicago to Orlando Flights

Return flight: Orlando – Chicago

Cheapflightsplus.com will find cheap United Airlines flights from Chicago to Orlando. Compare airline ticket prices and book air tickets starting from $117 from trusted online travel agencies, web sites and directly from airlines. Check flights schedule of United Airlines, arrivals and departure details below.

Find Cheap Airfare Chicago (IL) — Orlando (FL) by United Airlines

To find cheap tickets choose a day of your departure with attractive price on the graph below and click «Find flights». For round trip flights please click «Check prices for return flight». The cheapest airfare is in july: one-way - $117, two-way – $201.
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Below is a detailed 2025 flight schedule for today, tomorrow and all other days. It may vary depending on season and a day of the week of your desired trip. We recommend booking your itinerary at least 2 weeks prior your travel to get the best price and availability by the airline.
Departure Arrival Flight Details Flight Time Price
10:35 am — 2:27 pm
10:35 am — 2:27 pm UA2008 United Airlines
Chicago — Orlando
2h 52m
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from$118
11:02 am — 2:57 pm
11:02 am — 2:57 pm UA2479 United Airlines
Chicago — Orlando
2h 55m
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from$127
2:01 pm — 6:00 pm
2:01 pm — 6:00 pm UA2201 United Airlines
Chicago — Orlando
2h 59m
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from$118
2:15 pm — 6:06 pm
2:15 pm — 6:06 pm UA2042 United Airlines
Chicago — Orlando
2h 51m
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from$118
3:46 pm — 7:37 pm
3:46 pm — 7:37 pm UA2165 United Airlines
Chicago — Orlando
2h 51m
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from$117
5:50 pm — 9:46 pm
5:50 pm — 9:46 pm UA2039 United Airlines
Chicago — Orlando
2h 56m
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from$118
5:55 pm — 9:47 pm
5:55 pm — 9:47 pm UA1761 United Airlines
Chicago — Orlando
2h 52m
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from$117
5:55 pm — 9:47 pm
5:55 pm — 9:47 pm UA1911 United Airlines
Chicago — Orlando
2h 52m
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from$118
6:00 am — 9:47 am
6:00 am — 9:47 am UA2387 United Airlines
Chicago — Orlando
2h 47m
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from$118
7:10 am — 11:04 am
7:10 am — 11:04 am UA2280 United Airlines
Chicago — Orlando
2h 54m
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from$117
9:15 am — 1:09 pm
9:15 am — 1:09 pm UA2323 United Airlines
Chicago — Orlando
2h 54m
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from$118
10:43 am — 7:51 pm
10:43 am — 1:49 pm UA1030 United Airlines
Chicago — Washington D.C.
3h 41m stop
5:30 pm — 7:51 pm UA2463 United Airlines
Washington D.C. — Orlando
8h 8m
including layover
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from$250
11:46 am — 7:00 pm
11:46 am — 3:12 pm UA1205 United Airlines
Chicago — Newark
52m stop
4:04 pm — 7:00 pm UA1205 United Airlines
Newark — Orlando
6h 14m
including layover
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from$261
12:45 pm — 11:27 pm
12:45 pm — 3:40 pm UA2657 United Airlines
Chicago — Houston
4h 18m stop
7:58 pm — 11:27 pm UA1352 United Airlines
Houston — Orlando
9h 42m
including layover
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from$279
12:50 pm — 7:51 pm
12:50 pm — 3:52 pm UA1377 United Airlines
Chicago — Washington D.C.
1h 38m stop
5:30 pm — 7:51 pm UA2463 United Airlines
Washington D.C. — Orlando
6h 1m
including layover
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from$253
1:05 pm — 7:43 pm
1:05 pm — 4:10 pm UA2337 United Airlines
Chicago — Washington D.C.
1h 5m stop
5:15 pm — 7:43 pm UA2463 United Airlines
Washington D.C. — Orlando
5h 38m
including layover
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from$253
1:05 pm — 7:43 pm
1:05 pm — 4:10 pm UA1140 United Airlines
Chicago — Washington D.C.
1h 5m stop
5:15 pm — 7:43 pm UA2463 United Airlines
Washington D.C. — Orlando
5h 38m
including layover
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from$264
3:40 pm — 11:57 pm
3:40 pm — 7:14 pm UA2133 United Airlines
Chicago — Newark
1h 49m stop
9:03 pm — 11:57 pm UA212 United Airlines
Newark — Orlando
7h 17m
including layover
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from$292
4:07 pm — 11:27 pm
4:07 pm — 7:05 pm UA1124 United Airlines
Chicago — Houston
53m stop
7:58 pm — 11:27 pm UA1352 United Airlines
Houston — Orlando
6h 20m
including layover
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from$302
6:00 am — 5:02 pm
6:00 am — 9:15 am UA1658 United Airlines
Chicago — Newark
4h 57m stop
2:50 pm — 5:41 pm UA1213 United Airlines
Newark — Orlando
10h 2m
including layover
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from$271
7:35 pm — 10:27 am
+1 day
7:35 pm — 10:04 pm UA1641 United Airlines
Chicago — Cleveland
9h 56m stop
8:00 am — 10:27 am UA2636 United Airlines
Cleveland — Orlando
13h 52m
including layover
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from$208
8:50 am — 2:57 pm
8:52 am — 11:55 am UA2029 United Airlines
Chicago — Washington D.C.
40m stop
12:40 pm — 3:04 pm UA2206 United Airlines
Washington D.C. — Orlando
5h 7m
including layover
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from$250
8:52 am — 3:05 pm
8:52 am — 11:55 am UA2277 United Airlines
Chicago — Washington D.C.
45m stop
12:40 pm — 3:05 pm UA2206 United Airlines
Washington D.C. — Orlando
5h 13m
including layover
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from$252
9:50 pm — 10:52 am
+1 day
9:50 pm — 0:40 am UA1291 United Airlines
Chicago — Houston
6h 40m stop
7:20 am — 10:52 am UA2245 United Airlines
Houston — Orlando
12h 2m
including layover
Find flight
from$265
*Departure and arrival times are local. Last updated on 07/06/2025

Flight Information

There are 11 flights by United Airlines from Chicago to Orlando every week with departures from Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee. All flights arrive at Orlando Int., Walt Disney World, Herndon.

Departures start from 10:35 am to 9:50 pm. Nonstop flight is 2h 47m. The time difference between Chicago and Orlando is 1h.

  • The fastest flight 2h 47m
  • Average flight time 2h 52m
  • The earliest flight 10:35 am
  • The latest flight 9:50 pm
  • Distance 995 ml

The cheapest months for traveling to Orlando are september (from 117 $), august (from 118 $), october (from 122 $).

The most expensive and popular months are may (from 164 $), june (from 129 $), july (from 127 $).

The cheapest flight by United Airlines that our users were able to find is $117. This airfare is economy class on one-way UA2280 flight for September 27, 2025 leaving O'Hare International in Chicago at 7:10 am, it includes all taxes and additional fees.

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Other Popular Airlines on the Route

Besides United Airlines there are other 7 airline carriers between Chicago and Orlando. Please review schedules and prices from the most popular airlines to find the best airfare deals from Chicago to Orlando.

Nonstop flights

There are 20 direct flights every day from Chicago. Airlines and fares are below:

See more direct flights

Connecting Flights

List of flights with layovers (1 and more stops):

  • from $69
    Find
  • from $85
    Find
  • AS - Alaska Airlines
    from $238
    Find
  • SY - Sun Country Airlines
    from $168
    Find
  • HA - Hawaiian Airlines
    from $229
    Find
  • LF - flynordic
    from $243
    Find
  • G4 - Allegiant Air
    from $106
    Find
See more connecting flights

How to book an air ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected airfare.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

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