United Airlines Orlando to Chicago Flights
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
Cheap Flights from Orlando to Chicago by United Airlines
Price | Departure | Arrival | Flight Time | Airline | Flight |
---|---|---|---|---|---|
from $214 | 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 | 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 | 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 | 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 | 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 | 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 | 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 | 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 | 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 | 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 | 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 | 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 | 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 | 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 | 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 | 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 |
United Airlines Flight Schedule Orlando to Chicago
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 |
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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 |
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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 |
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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 |
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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 |
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.
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:
- from $78Find
- F9 - Frontier Airlinesfrom $89Find
Connecting Flights
List of flights with layovers (1 and more stops):
- from $84Find
- AS - Alaska Airlinesfrom $395Find
- F9 - Frontier Airlinesfrom $96Find
- MX - Mexicanafrom $218Find
- G4 - Allegiant Airfrom $195Find
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