United Airlines Orlando to Chicago Flights

Return flight: Chicago – Orlando

Cheapflightsplus.com will find cheap United Airlines flights from Orlando to Chicago. Compare airline ticket prices and book air tickets starting from $214 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 Orlando (FL) — Chicago (IL) 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 august: one-way - $214, two-way – $367.
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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
11:55 am — 4:48 pm
11:40 am — 1:56 pm UA1757 United Airlines
Orlando — Washington D.C.
1h 21m stop
3:35 pm — 4:48 pm UA1057 United Airlines
Washington D.C. — Chicago
5h 53m
including layover
Find flight
from$214
12:00 pm — 5:10 pm
12:00 pm — 1:32 pm UA774 United Airlines
Orlando — Houston
42m stop
2:14 pm — 5:10 pm UA2135 United Airlines
Houston — Chicago
6h 10m
including layover
Find flight
from$293
2:08 pm — 9:30 pm
2:08 pm — 3:40 pm UA2406 United Airlines
Orlando — Houston
2h 57m stop
6:40 pm — 9:33 pm UA520 United Airlines
Houston — Chicago
8h 22m
including layover
Find flight
from$291
5:09 pm — 8:39 am
+1 day
5:09 pm — 8:00 pm UA1557 United Airlines
Orlando — Newark
11h stop
7:00 am — 8:39 am UA2466 United Airlines
Newark — Chicago
16h 30m
including layover
Find flight
from$642
5:20 pm — 11:12 pm
5:20 pm — 6:58 pm UA2114 United Airlines
Orlando — Houston
1h 27m stop
9:30 pm — 0:13 am UA787 United Airlines
Houston — Chicago
6h 52m
including layover
Find flight
from$302
6:00 am — 2:55 pm
6:00 am — 8:38 am UA2607 United Airlines
Orlando — Newark
4h 40m stop
1:18 pm — 2:55 pm UA1832 United Airlines
Newark — Chicago
9h 55m
including layover
Find flight
from$608
7:05 pm — 11:30 pm
7:05 pm — 9:24 pm UA1742 United Airlines
Orlando — Washington D.C.
54m stop
10:18 pm — 11:30 pm UA1738 United Airlines
Washington D.C. — Chicago
5h 25m
including layover
Find flight
from$215
7:12 am — 12:26 pm
7:12 am — 8:44 am UA584 United Airlines
Orlando — Houston
46m stop
9:30 am — 12:26 pm UA2124 United Airlines
Houston — Chicago
6h 14m
including layover
Find flight
from$291
8:05 am — 2:33 pm
8:05 am — 10:16 am UA545 United Airlines
Orlando — Washington D.C.
3h 4m stop
1:20 pm — 2:33 pm UA2331 United Airlines
Washington D.C. — Chicago
7h 28m
including layover
Find flight
from$214
8:54 am — 2:55 pm
8:54 am — 11:32 am UA1227 United Airlines
Orlando — Newark
1h 46m stop
1:18 pm — 2:55 pm UA1832 United Airlines
Newark — Chicago
7h 1m
including layover
Find flight
from$293
9:15 am — 2:51 pm
9:15 am — 10:45 am UA2417 United Airlines
Orlando — Houston
1h 10m stop
11:55 am — 2:51 pm UA2417 United Airlines
Houston — Chicago
6h 36m
including layover
Find flight
from$261
9:15 am — 5:10 pm
9:15 am — 10:45 am UA2417 United Airlines
Orlando — Houston
3h 29m stop
2:14 pm — 5:10 pm UA2135 United Airlines
Houston — Chicago
8h 55m
including layover
Find flight
from$293
1:52 pm — 9:09 pm
1:52 pm — 4:11 pm UA688 United Airlines
Orlando — Washington D.C.
59m stop
5:10 pm — 6:44 pm UA3497 United Airlines
Washington D.C. — New York
46m stop
7:30 pm — 9:09 pm UA2627 United Airlines
New York — Chicago
8h 17m
including layover
Find flight
from$580
3:35 pm — 11:30 pm
3:35 pm — 6:26 pm UA2321 United Airlines
Orlando — Newark
1h 19m stop
7:45 pm — 9:13 pm UA1397 United Airlines
Newark — Washington D.C.
1h 5m stop
10:18 pm — 11:30 pm UA1738 United Airlines
Washington D.C. — Chicago
8h 55m
including layover
Find flight
from$674
4:10 pm — 11:09 pm
4:10 pm — 6:29 pm UA413 United Airlines
Orlando — Washington D.C.
30m stop
6:59 pm — 8:30 pm UA619 United Airlines
Washington D.C. — New York
1h stop
9:30 pm — 11:09 pm UA210 United Airlines
New York — Chicago
7h 59m
including layover
Find flight
from$580
*Departure and arrival times are local. Last updated on 07/27/2025

Flight Information

There are 26 flights by United Airlines from Orlando to Chicago every week with departures from Orlando Int., Walt Disney World, Herndon. All flights arrive at Chicago FSS, Midway, O'Hare International, Chicago NAS, Merrill C Meigs (closed), Dupage County, Pal-Waukee.

Departures start from 11:55 am to 9:50 am. Nonstop flight is 5h 25m. The time difference between Orlando and Chicago is 1h.

  • The fastest flight 5h 25m
  • Average flight time 8h 22m
  • The earliest flight 11:55 am
  • The latest flight 9:50 am
  • Distance 995 ml

The cheapest months for traveling to Chicago are may (from 214 $), august (from 261 $), july (from 263 $).

The most expensive and popular months are june (from 293 $), july (from 263 $), august (from 261 $).

The cheapest flight by United Airlines that our users were able to find is $214. This airfare is economy class on one-way UA1757 flight for June 4, 2025 leaving Orlando Int. in Orlando at 11:55 am, it includes all taxes and additional fees.

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Other Popular Airlines on the Route

Besides United Airlines there are other 5 airline carriers between Orlando and Chicago. Please review schedules and prices from the most popular airlines to find the best airfare deals from Orlando to Chicago.

Nonstop flights

There are 3 direct flights every day from Orlando. Airlines and fares are below:

See more direct flights

Connecting Flights

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

  • from $84
    Find
  • AS - Alaska Airlines
    from $395
    Find
  • F9 - Frontier Airlines
    from $96
    Find
  • MX - Mexicana
    from $218
    Find
  • G4 - Allegiant Air
    from $195
    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.
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  • 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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