United Airlines Orlando to Chicago Flights

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Cheapflightsplus.com will find cheap United Airlines flights from Orlando to Chicago. Compare airline ticket prices and book air tickets starting from $134 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 march: one-way - $134, two-way – $230.

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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 $134. The fastest nonstop flight takes 3h 2m. The fastest connecting flight — 5h 5m.

Price	Departure	Arrival	Flight Time	Airline	Flight
from $135 Find flight	4:33 pm Orlando Orlando Int.	6:35 pm Chicago O'Hare International	3h 2m	United Airlines	UA1828
from $136 Find flight	7:30 am Orlando Orlando Int.	9:33 am Chicago O'Hare International	3h 3m	United Airlines	UA2673
from $136 Find flight	9:30 am Orlando Orlando Int.	11:33 am Chicago O'Hare International	3h 3m	United Airlines	UA395
from $136 Find flight	10:30 am Orlando Orlando Int.	12:33 pm Chicago O'Hare International	3h 3m	United Airlines	UA1485
from $136 Find flight	12:30 pm Orlando Orlando Int.	2:32 pm Chicago O'Hare International	3h 2m	United Airlines	UA2475
from $157 Find flight	9:30 am Orlando Orlando Int.	11:33 am Chicago O'Hare International	3h 3m	United Airlines	UA2341
from $157 Find flight	6:00 pm Orlando Orlando Int.	8:03 pm Chicago O'Hare International	3h 3m	United Airlines	UA2000
from $159 Find flight	11:00 am Orlando Orlando Int.	1:06 pm Chicago O'Hare International	3h 6m	United Airlines	UA374
from $159 Find flight	2:35 pm Orlando Orlando Int.	4:38 pm Chicago O'Hare International	3h 3m	United Airlines	UA2061
from $199 Find flight	11:00 am Orlando Orlando Int.	1:03 pm Chicago O'Hare International	3h 3m	United Airlines	UA503
from $353 Find flight	2:25 pm Orlando Orlando Int.	4:38 pm Chicago O'Hare International	3h 13m	United Airlines	UA1492
from $134 Find flight	9:35 am Orlando Orlando Int.	6:41 pm Chicago O'Hare International	10h 6m layover 5h 25m - Miami	United Airlines	UA3053 NK157
from $157 Find flight	7:15 pm Orlando Orlando Int.	11:20 pm Chicago O'Hare International	5h 5m layover 0h 51m - Washington D.C.	United Airlines	UA1997 UA1738
from $209 Find flight	3:16 pm Orlando Orlando Int.	11:20 pm Chicago O'Hare International	9h 4m layover 4h 46m - Washington D.C.	United Airlines	UA1245 UA1738
from $216 Find flight	9:35 am Orlando Orlando Int.	7:53 pm Chicago O'Hare International	11h 18m layover 4h 41m - Miami 1h 15m - Atlanta	United Airlines	UA3053 DL1582 DL2879
from $538 Find flight	12:30 pm Orlando Orlando Int.	11:20 pm Chicago O'Hare International	11h 50m layover 3h 42m - Newark 1h 58m - Washington D.C.	United Airlines	UA1768 UA558 UA1738

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*Departure and arrival times are local. Prices are for one-way flights. Information refreshed on 03/10/2025

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
10:30 am — 12:33 pm	10:30 am — 12:33 pm UA1485 United Airlines Orlando — Chicago	3h 3m	Find flight from$136
11:00 am — 1:06 pm	11:00 am — 1:06 pm UA374 United Airlines Orlando — Chicago	3h 6m	Find flight from$159
11:00 am — 1:03 pm	11:00 am — 1:03 pm UA503 United Airlines Orlando — Chicago	3h 3m	Find flight from$199
12:30 pm — 2:32 pm	12:30 pm — 2:32 pm UA2475 United Airlines Orlando — Chicago	3h 2m	Find flight from$136
2:25 pm — 4:38 pm	2:25 pm — 4:38 pm UA1492 United Airlines Orlando — Chicago	3h 13m	Find flight from$353
2:35 pm — 4:38 pm	2:35 pm — 4:38 pm UA2061 United Airlines Orlando — Chicago	3h 3m	Find flight from$159
4:33 pm — 6:35 pm	4:33 pm — 6:35 pm UA1828 United Airlines Orlando — Chicago	3h 2m	Find flight from$135
6:00 pm — 8:03 pm	6:00 pm — 8:03 pm UA2000 United Airlines Orlando — Chicago	3h 3m	Find flight from$157
7:30 am — 9:33 am	7:30 am — 9:33 am UA2673 United Airlines Orlando — Chicago	3h 3m	Find flight from$136
7:34 pm — 9:44 pm	7:34 pm — 9:44 pm UA2677 United Airlines Orlando — Chicago	3h 10m	Find flight from$161
9:30 am — 11:33 am	9:30 am — 11:33 am UA395 United Airlines Orlando — Chicago	3h 3m	Find flight from$136
9:30 am — 11:33 am	9:30 am — 11:33 am UA2341 United Airlines Orlando — Chicago	3h 3m	Find flight from$157
10:23 am — 4:03 pm	10:23 am — 1:02 pm UA1493 United Airlines Orlando — Newark 1h 27m stop 2:29 pm — 4:03 pm UA323 United Airlines Newark — Chicago	6h 40m including layover	Find flight from$352
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$170
1:17 pm — 11:00 pm	1:17 pm — 4:00 pm UA2310 United Airlines Orlando — Newark 5h 29m stop 9:29 pm — 11:00 pm UA1308 United Airlines Newark — Chicago	10h 43m including layover	Find flight from$258
1:17 pm — 9:22 pm	1:17 pm — 4:00 pm UA2310 United Airlines Orlando — Newark 3h 43m stop 7:43 pm — 9:22 pm UA546 United Airlines Newark — Chicago	9h 5m including layover	Find flight from$338
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$170
3:16 pm — 11:20 pm	3:16 pm — 5:30 pm UA1245 United Airlines Orlando — Washington D.C. 4h 46m stop 10:16 pm — 11:20 pm UA1738 United Airlines Washington D.C. — Chicago	9h 4m including layover	Find flight from$209
3:20 pm — 9:22 pm	3:18 pm — 6:05 pm UA2321 United Airlines Orlando — Newark 1h 36m stop 7:43 pm — 9:22 pm UA546 United Airlines Newark — Chicago	7h 2m including layover	Find flight from$338
4:20 pm — 11:20 pm	4:20 pm — 6:32 pm UA1832 United Airlines Orlando — Washington D.C. 3h 44m stop 10:16 pm — 11:20 pm UA1738 United Airlines Washington D.C. — Chicago	8h including layover	Find flight from$169
5:18 pm — 11:00 pm	5:18 pm — 8:01 pm UA2430 United Airlines Orlando — Newark 1h 28m stop 9:29 pm — 11:00 pm UA1308 United Airlines Newark — Chicago	6h 42m including layover	Find flight from$318
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$170
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$167
7:15 pm — 11:20 pm	7:15 pm — 9:25 pm UA1997 United Airlines Orlando — Washington D.C. 51m stop 10:16 pm — 11:20 pm UA1738 United Airlines Washington D.C. — Chicago	5h 5m including layover	Find flight from$157
8:00 am — 6:54 pm	8:00 am — 10:40 am UA370 United Airlines Orlando — Newark 6h 35m stop 5:15 pm — 6:54 pm UA661 United Airlines Newark — Chicago	11h 54m including layover	Find flight from$258
8:50 am — 2:19 pm	8:50 am — 11:02 am UA1808 United Airlines Orlando — Washington D.C. 2h 3m stop 1:05 pm — 2:19 pm UA2331 United Airlines Washington D.C. — Chicago	6h 29m including layover	Find flight from$217
9:35 am — 6:41 pm	9:35 am — 10:55 am UA3053 United Airlines Orlando — Miami 5h 25m stop 4:20 pm — 6:41 pm NK157 Spirit Airlines Miami — Chicago	10h 6m including layover	Find flight from$134
9:35 am — 9:08 pm	9:35 am — 10:55 am UA3053 United Airlines Orlando — Miami 7h 50m stop 6:45 pm — 9:08 pm NK7 Spirit Airlines Miami — Chicago	12h 33m including layover	Find flight from$134

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

*Departure and arrival times are local. Last updated on 03/10/2025

Flight Information

There are 12 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 10:23 am to 9:57 am. Nonstop flight is 3h 2m. The time difference between Orlando and Chicago is 1h.

The fastest flight 3h 2m
Average flight time 3h 3m
The earliest flight 10:23 am
The latest flight 9:57 am
Distance 995 ml

The cheapest months for traveling to Chicago are november (from 134 $), january (from 135 $), february (from 135 $).

The most expensive and popular months are december (from 136 $), february (from 135 $), january (from 135 $).

The cheapest flight by United Airlines that our users were able to find is $134. This airfare is economy class on one-way UA3053 flight for November 12, 2024 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:

Aerospatiale/Alenia ATR 72

from $134

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Boeing 737 MAX 9

from $169

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Boeing 757-300

from $251

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Boeing 737-900

from $258

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Boeing 737

from $338

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Boeing 737 MAX 8

from $352

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Boeing 757

from $360

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Boeing 757-200

from $360

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Boeing 737-800

from $567

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Other Popular Airlines on the Route

Besides United Airlines there are other 13 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 33 direct flights every day from Orlando. Airlines and fares are below:

NK - Spirit Airlines

from $88

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AA - American Airlines

from $156

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F9 - Frontier Airlines

from $49

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WN - Southwest Airlines

from $160

Find

See more direct flights

Connecting Flights

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

NK - Spirit Airlines

from $48

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AA - American Airlines

from $179

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SY - Sun Country Airlines

from $128

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DL - Delta Air Lines Inc.

from $121

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MX - Mexicana

from $152

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AM - Aeromexico

from $414

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AS - Alaska Airlines

from $238

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F9 - Frontier Airlines

from $62

Find
B6 - JetBlue

from $561

Find
WN - Southwest Airlines

from $155

Find
3M - Gulfstream International Airlines

from $441

Find

See more connecting flights

How to book an air ticket yourself?

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