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 $119 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 january: one-way - $119, two-way – $204.
Direct flights
Check prices for return flight
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 $119. The fastest nonstop flight takes 3h 2m. The fastest connecting flight — 5h 42m.
| Price | Departure | Arrival | Flight Time | Airline | Flight |
|---|---|---|---|---|---|
| from $119 | 4:33 pm Orlando Orlando Int. | 6:35 pm Chicago O'Hare International | 3h 2m | United Airlines | UA1828 |
| from $140 | 11:00 am Orlando Orlando Int. | 1:06 pm Chicago O'Hare International | 3h 6m | United Airlines | UA374 |
| from $140 | 2:35 pm Orlando Orlando Int. | 4:38 pm Chicago O'Hare International | 3h 3m | United Airlines | UA2061 |
| from $142 | 7:34 pm Orlando Orlando Int. | 9:44 pm Chicago O'Hare International | 3h 10m | United Airlines | UA2677 |
| from $310 | 2:25 pm Orlando Orlando Int. | 4:38 pm Chicago O'Hare International | 3h 13m | United Airlines | UA1492 |
| from $147 | 6:57 pm Orlando Orlando Int. | 0:15 am+1 день Chicago O'Hare International | 6h 18m layover 0h 50m - Houston | United Airlines | UA1692 UA1692 |
| from $150 | 2:13 pm Orlando Orlando Int. | 6:55 pm Chicago O'Hare International | 5h 42m layover 1h 6m - Washington D.C. | United Airlines | UA2065 UA1117 |
| from $150 | 9:00 am Orlando Orlando Int. | 2:34 pm Chicago O'Hare International | 6h 34m layover 2h 2m - Washington D.C. | United Airlines | UA1689 UA1193 |
| from $150 | 12:35 pm Orlando Orlando Int. | 6:55 pm Chicago O'Hare International | 7h 20m layover 2h 48m - Washington D.C. | United Airlines | UA1660 UA1117 |
| from $150 | 5:46 pm Orlando Orlando Int. | 11:15 pm Chicago O'Hare International | 6h 29m layover 2h 11m - Washington D.C. | United Airlines | UA1030 UA1738 |
| from $191 | 9:35 am Orlando Orlando Int. | 10:52 am+1 день Chicago O'Hare International | 26h 17m layover 21h 30m - Miami | United Airlines | UA3053 UA1878 |
| from $191 | 7:10 pm Orlando Orlando Int. | 6:49 pm+1 день Chicago O'Hare International | 24h 39m layover 19h 55m - Miami | United Airlines | UA3069 UA672 |
| from $191 | 7:10 pm Orlando Orlando Int. | 10:52 am+1 день Chicago O'Hare International | 16h 42m layover 11h 55m - Miami | United Airlines | UA3069 UA1878 |
| from $202 | 4:28 pm Orlando Orlando Int. | 11:22 pm Chicago O'Hare International | 7h 54m layover 3h 36m - Washington D.C. | United Airlines | UA413 UA1738 |
| from $232 | 6:00 am Orlando Orlando Int. | 6:54 pm Chicago O'Hare International | 13h 54m layover 8h 25m - Newark | United Airlines | UA2607 UA661 |
| from $197 | 9:35 am Orlando Orlando Int. | 11:22 pm Chicago O'Hare International | 14h 47m layover 7h 15m - Miami 1h 32m - Washington D.C. | United Airlines | UA3053 UA2071 UA1738 |
Show All Flights
*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 01/08/2025
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 | Arrival | Flight Details | Flight Time | Price |
|---|---|---|---|---|
|
11:00 am — 1:06 pm
|
11:00 am — 1:06 pm
UA374
United Airlines
Orlando — Chicago
|
3h 6m |
Find flight
from$140 |
|
|
2:25 pm — 4:38 pm
|
2:25 pm — 4:38 pm
UA1492
United Airlines
Orlando — Chicago
|
3h 13m |
Find flight
from$310 |
|
|
2:35 pm — 4:38 pm
|
2:35 pm — 4:38 pm
UA2061
United Airlines
Orlando — Chicago
|
3h 3m |
Find flight
from$140 |
|
|
4:33 pm — 6:35 pm
|
4:33 pm — 6:35 pm
UA1828
United Airlines
Orlando — Chicago
|
3h 2m |
Find flight
from$119 |
|
|
7:34 pm — 9:44 pm
|
7:34 pm — 9:44 pm
UA2677
United Airlines
Orlando — Chicago
|
3h 10m |
Find flight
from$142 |
|
|
11:56 am — 5:10 pm
|
11:56 am — 1:40 pm
UA774
United Airlines
Orlando — Houston
40m stop
2:20 pm — 5:10 pm
UA1293
United Airlines
Houston — Chicago
|
6h 14m including layover |
Find flight
from$316 |
|
|
12:35 pm — 6:55 pm
|
12:35 pm — 2:48 pm
UA1660
United Airlines
Orlando — Washington D.C.
2h 48m stop
5:36 pm — 6:55 pm
UA1117
United Airlines
Washington D.C. — Chicago
|
7h 20m including layover |
Find flight
from$150 |
|
|
12:55 pm — 6:21 pm
|
12:55 pm — 2:20 pm
UA3071
United Airlines
Orlando — Key West
1h 30m stop
3:50 pm — 6:21 pm
UA770
United Airlines
Key West — Chicago
|
6h 26m including layover |
Find flight
from$254 |
|
|
1:40 pm — 7:10 pm
|
1:40 pm — 3:23 pm
UA2009
United Airlines
Orlando — Houston
57m stop
4:20 pm — 7:10 pm
UA2293
United Airlines
Houston — Chicago
|
6h 30m including layover |
Find flight
from$316 |
|
|
2:13 pm — 6:55 pm
|
2:13 pm — 4:30 pm
UA2065
United Airlines
Orlando — Washington D.C.
1h 6m stop
5:36 pm — 6:55 pm
UA1117
United Airlines
Washington D.C. — Chicago
|
5h 42m including layover |
Find flight
from$150 |
|
|
4:28 pm — 11:22 pm
|
4:20 pm — 6:32 pm
UA413
United Airlines
Orlando — Washington D.C.
3h 36m stop
10:16 pm — 11:20 pm
UA1738
United Airlines
Washington D.C. — Chicago
|
7h 54m including layover |
Find flight
from$202 |
|
|
5:40 pm — 10:57 pm
|
5:40 pm — 8:29 pm
UA1557
United Airlines
Orlando — Newark
56m stop
9:25 pm — 10:57 pm
UA1308
United Airlines
Newark — Chicago
|
6h 17m including layover |
Find flight
from$316 |
|
|
5:46 pm — 11:15 pm
|
5:46 pm — 7:58 pm
UA1030
United Airlines
Orlando — Washington D.C.
2h 11m stop
10:09 pm — 11:15 pm
UA1738
United Airlines
Washington D.C. — Chicago
|
6h 29m including layover |
Find flight
from$150 |
|
|
6:00 am — 6:54 pm
|
6:00 am — 8:38 am
UA2607
United Airlines
Orlando — Newark
8h 25m stop
5:15 pm — 6:54 pm
UA661
United Airlines
Newark — Chicago
|
13h 54m including layover |
Find flight
from$232 |
|
|
6:57 pm — 0:15 am
+1 day
|
6:57 pm — 8:48 pm
UA1692
United Airlines
Orlando — Houston
50m stop
9:38 pm — 0:15 am
UA1692
United Airlines
Houston — Chicago
|
6h 18m including layover |
Find flight
from$147 |
|
|
7:10 pm — 6:49 pm
+1 day
|
7:10 pm — 8:30 pm
UA3069
United Airlines
Orlando — Miami
19h 55m stop
4:25 pm — 6:49 pm
UA672
United Airlines
Miami — Chicago
|
24h 39m including layover |
Find flight
from$191 |
|
|
8:00 am — 6:54 pm
|
8:00 am — 10:41 am
UA2727
United Airlines
Orlando — Newark
6h 27m stop
5:08 pm — 6:54 pm
UA661
United Airlines
Newark — Chicago
|
11h 54m including layover |
Find flight
from$232 |
|
|
8:00 am — 8:25 pm
|
8:00 am — 10:41 am
UA2727
United Airlines
Orlando — Newark
8h 2m stop
6:43 pm — 8:25 pm
UA254
United Airlines
Newark — Chicago
|
13h 25m including layover |
Find flight
from$232 |
|
|
9:00 am — 2:34 pm
|
9:00 am — 11:13 am
UA1689
United Airlines
Orlando — Washington D.C.
2h 2m stop
1:15 pm — 2:34 pm
UA1193
United Airlines
Washington D.C. — Chicago
|
6h 34m including layover |
Find flight
from$150 |
|
|
9:35 am — 10:52 am
+1 day
|
9:35 am — 10:55 am
UA3053
United Airlines
Orlando — Miami
21h 30m stop
8:25 am — 10:52 am
UA1878
United Airlines
Miami — Chicago
|
26h 17m including layover |
Find flight
from$191 |
|
*Departure and arrival times are local. Last updated on 01/08/2025
Flight Information
There are 5 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 11:00 am to 9:35 am. Nonstop flight is 3h 2m. The time difference between Orlando and Chicago is 1h.
- The fastest flight 3h 2m
- Average flight time 3h 6m
- The earliest flight 11:00 am
- The latest flight 9:35 am
- Distance 995 ml
The cheapest months for traveling to Chicago are january (from 119 $), february (from 119 $), december (from 120 $).
The most expensive and popular months are november (from 139 $), december (from 120 $), february (from 119 $).
The cheapest flight by United Airlines that our users were able to find is $119. This airfare is economy class on one-way UA1828 flight for January 22, 2025 leaving Orlando Int. in Orlando at 4:33 pm, 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:
- Boeing 737-900from $316Find
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 11 direct flights every day from Orlando. Airlines and fares are below:
- from $73Find
- from $115Find
See more direct flights
Connecting Flights
List of flights with layovers (1 and more stops):
- from $221Find
- from $57Find
- from $91Find
- MX - Mexicanafrom $144Find
- Y4 - Volarisfrom $325Find
- AM - Aeromexicofrom $426Find
See more connecting flights
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.