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 $86 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 june: one-way - $86, two-way – $147.

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Cheap Flights from Orlando to Chicago by United Airlines

Look at the list of plane tickets for the most popular direct and connecting flights by United Airlines, their prices start from $86. The fastest nonstop flight takes 3h 5m. The fastest connecting flight — 4h 52m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $86 Find flight	9:35 am Orlando Orlando Int.	11:41 am Chicago O'Hare International	3h 6m	United Airlines	UA2341
from $86 Find flight	7:20 am Orlando Orlando Int.	9:26 am Chicago O'Hare International	3h 6m	United Airlines	UA1097
from $86 Find flight	11:00 am Orlando Orlando Int.	1:06 pm Chicago O'Hare International	3h 6m	United Airlines	UA2207
from $86 Find flight	4:26 pm Orlando Orlando Int.	6:32 pm Chicago O'Hare International	3h 6m	United Airlines	UA1828
from $86 Find flight	7:15 am Orlando Orlando Int.	9:20 am Chicago O'Hare International	3h 5m	United Airlines	UA2673
from $87 Find flight	12:16 pm Orlando Orlando Int.	2:22 pm Chicago O'Hare International	3h 6m	United Airlines	UA2475
from $87 Find flight	2:30 pm Orlando Orlando Int.	4:36 pm Chicago O'Hare International	3h 6m	United Airlines	UA1403
from $92 Find flight	6:16 pm Orlando Orlando Int.	8:21 pm Chicago O'Hare International	3h 5m	United Airlines	UA2000
from $103 Find flight	7:30 am Orlando Orlando Int.	9:36 am Chicago O'Hare International	3h 6m	United Airlines	UA2657
from $158 Find flight	8:00 am Orlando Orlando Int.	2:33 pm Chicago O'Hare International	7h 33m layover 3h 9m - Washington D.C.	United Airlines	UA1395 UA2331
from $158 Find flight	7:06 pm Orlando Orlando Int.	11:30 pm Chicago O'Hare International	5h 24m layover 0h 54m - Washington D.C.	United Airlines	UA504 UA1738
from $182 Find flight	1:40 pm Orlando Orlando Int.	11:30 pm Chicago O'Hare International	10h 50m layover 6h 20m - Washington D.C.	United Airlines	UA2065 UA1738
from $185 Find flight	1:05 pm Orlando Orlando Int.	6:30 pm Chicago O'Hare International	6h 25m layover 1h 59m - Washington D.C.	United Airlines	UA1757 UA2497
from $185 Find flight	1:05 pm Orlando Orlando Int.	7:55 pm Chicago O'Hare International	7h 50m layover 3h 31m - Washington D.C.	United Airlines	UA1757 UA2304
from $185 Find flight	7:13 pm Orlando Orlando Int.	11:15 pm Chicago O'Hare International	5h 2m layover 0h 45m - Washington D.C.	United Airlines	UA496 UA1738
from $210 Find flight	11:43 am Orlando Orlando Int.	8:09 pm Chicago O'Hare International	9h 26m layover 5h 19m - Cleveland	United Airlines	UA486 UA5522

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 06/02/2025

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
11:00 am — 1:06 pm	11:00 am — 1:06 pm UA2207 United Airlines Orlando — Chicago	3h 6m	Find flight from$86
12:16 pm — 2:22 pm	12:16 pm — 2:22 pm UA2475 United Airlines Orlando — Chicago	3h 6m	Find flight from$87
2:30 pm — 4:36 pm	2:30 pm — 4:36 pm UA1403 United Airlines Orlando — Chicago	3h 6m	Find flight from$87
4:26 pm — 6:32 pm	4:26 pm — 6:32 pm UA1828 United Airlines Orlando — Chicago	3h 6m	Find flight from$86
6:16 pm — 8:21 pm	6:16 pm — 8:21 pm UA2000 United Airlines Orlando — Chicago	3h 5m	Find flight from$92
7:15 am — 9:20 am	7:15 am — 9:20 am UA2673 United Airlines Orlando — Chicago	3h 5m	Find flight from$86
7:20 am — 9:26 am	7:20 am — 9:26 am UA1097 United Airlines Orlando — Chicago	3h 6m	Find flight from$86
7:30 am — 9:36 am	7:30 am — 9:36 am UA2657 United Airlines Orlando — Chicago	3h 6m	Find flight from$103
9:35 am — 11:41 am	9:35 am — 11:41 am UA2341 United Airlines Orlando — Chicago	3h 6m	Find flight from$86
10:00 am — 6:34 pm	10:00 am — 12:39 pm UA2120 United Airlines Orlando — Newark 4h 15m stop 4:54 pm — 6:34 pm UA661 United Airlines Newark — Chicago	9h 34m including layover	Find flight from$200
10:00 am — 4:35 pm	10:00 am — 12:39 pm UA2120 United Airlines Orlando — Newark 2h 16m stop 2:55 pm — 4:35 pm UA2009 United Airlines Newark — Chicago	7h 35m including layover	Find flight from$213
11:43 am — 8:11 pm	11:43 am — 2:08 pm UA486 United Airlines Orlando — Cleveland 5h 29m stop 7:37 pm — 8:11 pm UA2443 United Airlines Cleveland — Chicago	9h 28m including layover	Find flight from$191
12:00 pm — 9:33 pm	12:00 pm — 1:32 pm UA774 United Airlines Orlando — Houston 5h 8m stop 6:40 pm — 9:33 pm UA520 United Airlines Houston — Chicago	10h 33m including layover	Find flight from$189
1:05 pm — 6:30 pm	11:40 am — 1:56 pm UA1757 United Airlines Orlando — Washington D.C. 1h 59m stop 5:10 pm — 6:37 pm UA2497 United Airlines Washington D.C. — Chicago	6h 25m including layover	Find flight from$185
1:40 pm — 11:30 pm	1:40 pm — 3:59 pm UA2065 United Airlines Orlando — Washington D.C. 6h 20m stop 10:19 pm — 11:30 pm UA1738 United Airlines Washington D.C. — Chicago	10h 50m including layover	Find flight from$182
2:08 pm — 9:33 pm	2:08 pm — 3:40 pm UA2406 United Airlines Orlando — Houston 3h stop 6:40 pm — 9:33 pm UA520 United Airlines Houston — Chicago	8h 25m including layover	Find flight from$213
3:41 pm — 0:15 am +1 day	3:41 pm — 5:20 pm UA2215 United Airlines Orlando — Houston 4h 14m stop 9:34 pm — 0:15 am UA2234 United Airlines Houston — Chicago	9h 34m including layover	Find flight from$213
3:43 pm — 11:12 pm	3:43 pm — 5:21 pm UA2215 United Airlines Orlando — Houston 3h 4m stop 8:25 pm — 11:12 pm UA2013 United Airlines Houston — Chicago	8h 29m including layover	Find flight from$215
4:03 pm — 7:55 pm	4:03 pm — 6:12 pm UA413 United Airlines Orlando — Washington D.C. 35m stop 6:47 pm — 7:55 pm UA2304 United Airlines Washington D.C. — Chicago	4h 52m including layover	Find flight from$185
5:03 pm — 11:12 pm	5:03 pm — 6:41 pm UA1696 United Airlines Orlando — Houston 1h 44m stop 8:25 pm — 11:12 pm UA2013 United Airlines Houston — Chicago	7h 9m including layover	Find flight from$213
5:04 pm — 10:41 pm	5:04 pm — 6:43 pm UA787 United Airlines Orlando — Houston 1h 7m stop 7:50 pm — 10:41 pm UA787 United Airlines Houston — Chicago	6h 37m including layover	Find flight from$193
6:00 am — 11:49 am	6:00 am — 8:37 am UA1343 United Airlines Orlando — Newark 1h 33m stop 10:10 am — 11:49 am UA1525 United Airlines Newark — Chicago	6h 49m including layover	Find flight from$213
8:00 am — 2:33 pm	8:00 am — 10:11 am UA1395 United Airlines Orlando — Washington D.C. 3h 9m stop 1:20 pm — 2:33 pm UA2331 United Airlines Washington D.C. — Chicago	7h 33m including layover	Find flight from$158
8:00 am — 6:40 pm	8:00 am — 10:11 am UA1395 United Airlines Orlando — Washington D.C. 7h 2m stop 5:13 pm — 6:40 pm UA2497 United Airlines Washington D.C. — Chicago	11h 40m including layover	Find flight from$182
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$192

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

*Departure and arrival times are local. Last updated on 06/02/2025

Flight Information

There are 9 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 10:00 am to 9:50 am. Nonstop flight is 3h 5m. The time difference between Orlando and Chicago is 1h.

The fastest flight 3h 5m
Average flight time 3h 6m
The earliest flight 10:00 am
The latest flight 9:50 am
Distance 995 ml

The cheapest months for traveling to Chicago are october (from 115 $), september (from 115 $), august (from 115 $).

The most expensive and popular months are may (from 199 $), june (from 157 $), july (from 124 $).

The cheapest flight by United Airlines that our users were able to find is $86. This airfare is economy class on one-way UA2341 flight for October 7, 2025 leaving Orlando Int. in Orlando at 9:35 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 6 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 18 direct flights every day from Orlando. Airlines and fares are below:

NK - Spirit Airlines

from $38

Find
F9 - Frontier Airlines

from $45

Find

See more direct flights

Connecting Flights

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

NK - Spirit Airlines

from $55

Find
AS - Alaska Airlines

from $177

Find
F9 - Frontier Airlines

from $53

Find
SY - Sun Country Airlines

from $120

Find
MX - Mexicana

from $159

Find
G4 - Allegiant Air

from $76

Find

See more connecting flights

How to book an air ticket yourself?

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