United Airlines Orlando to Chicago Flights

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Best Airfare Price Calendar Flights Schedule

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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Cheap Flights from Orlando to Chicago by United Airlines

Look at the list of plane tickets for the most connecting flights by United Airlines, their prices start from $214. There’re no direct flights. The fastest connecting flight – 5h 25m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $214 Find flight	11:55 am Orlando Orlando Int.	4:48 pm Chicago O'Hare International	5h 53m layover 1h 21m - Washington D.C.	United Airlines	UA1757 UA1057
from $214 Find flight	8:05 am Orlando Orlando Int.	2:33 pm Chicago O'Hare International	7h 28m layover 3h 4m - Washington D.C.	United Airlines	UA545 UA2331
from $215 Find flight	7:05 pm Orlando Orlando Int.	11:30 pm Chicago O'Hare International	5h 25m layover 0h 54m - Washington D.C.	United Airlines	UA1742 UA1738
from $261 Find flight	9:15 am Orlando Orlando Int.	2:51 pm Chicago O'Hare International	6h 36m layover 1h 10m - Houston	United Airlines	UA2417 UA2417
from $291 Find flight	7:12 am Orlando Orlando Int.	12:26 pm Chicago O'Hare International	6h 14m layover 0h 46m - Houston	United Airlines	UA584 UA2124
from $291 Find flight	2:08 pm Orlando Orlando Int.	9:30 pm Chicago O'Hare International	8h 22m layover 2h 57m - Houston	United Airlines	UA2406 UA520
from $293 Find flight	12:00 pm Orlando Orlando Int.	5:10 pm Chicago O'Hare International	6h 10m layover 0h 42m - Houston	United Airlines	UA774 UA2135
from $293 Find flight	9:50 am Orlando Orlando Int.	2:55 pm Chicago O'Hare International	6h 5m layover 0h 50m - Newark	United Airlines	UA2120 UA1832
from $293 Find flight	8:54 am Orlando Orlando Int.	2:55 pm Chicago O'Hare International	7h 1m layover 1h 46m - Newark	United Airlines	UA1227 UA1832
from $293 Find flight	7:12 am Orlando Orlando Int.	2:51 pm Chicago O'Hare International	8h 39m layover 3h 11m - Houston	United Airlines	UA584 UA2417
from $302 Find flight	5:20 pm Orlando Orlando Int.	11:12 pm Chicago O'Hare International	6h 52m layover 1h 27m - Houston	United Airlines	UA2114 UA787
from $307 Find flight	8:05 am Orlando Orlando Int.	4:48 pm Chicago O'Hare International	9h 43m layover 5h 19m - Washington D.C.	United Airlines	UA545 UA1057
from $338 Find flight	7:15 pm Orlando Orlando Int.	0:13 am+1 день Chicago O'Hare International	5h 58m layover 0h 43m - Houston	United Airlines	UA1475 UA2013
from $550 Find flight	7:05 pm Orlando Orlando Int.	6:30 am+1 день Chicago O'Hare International	12h 25m layover 0h 52m - Washington D.C. 6h 4m - Detroit	United Airlines	UA1742 UA3623 UA3442
from $550 Find flight	7:05 pm Orlando Orlando Int.	7:46 am+1 день Chicago O'Hare International	13h 41m layover 0h 52m - Washington D.C. 7h 19m - Detroit	United Airlines	UA1742 UA3623 UA5353
from $580 Find flight	1:52 pm Orlando Orlando Int.	9:09 pm Chicago O'Hare International	8h 17m layover 0h 59m - Washington D.C. 0h 46m - New York	United Airlines	UA688 UA3497 UA2627

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 07/27/2025

United Airlines Flight Schedule Orlando to Chicago

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	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	Arrival	Flight Details	Flight Time	Price
		stop stop	including layover	Find flight from$

*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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United Airlines Airplanes on the Route

List of the most popular United Airlines airplanes flying from Orlando to Chicago:

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:

NK - Spirit Airlines

from $78

Find
F9 - Frontier Airlines

from $89

Find

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Connecting Flights

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

NK - Spirit Airlines

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?

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