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Find cheap United Airlines flights to Chicago from C$ 188

1 adult
0 bags
Thu 30/5
Thu 6/6

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Good to know

Low season

January

High season

August

Cheapest flight

C$ 188

Average price round-trip

C$ 644

Good deal one-way

C$ 434
Best time to beat the crowds (16% less expensive on average)
Most popular time to fly and prices are also 5% lower on average.
Flight from Calgary to Chicago O'Hare Airport
(avg. price over the last 2 weeks)
or less

When to book flights with United Airlines to Chicago

Average price per month
Flight prices as travel date approaches

FAQs for flying to Chicago with United Airlines

  • Which other airlines fly to Chicago?

    Along with United Airlines, you can also fly to Chicago with Porter Airlines and Porter Airlines.

  • How much is a flight to Chicago with United Airlines?

    On average, United Airlines flights to Chicago cost C$ 331 one-way.

  • Which airport do United Airlines flights to Chicago fly into?

    United Airlines flights to Chicago will fly into either Chicago O'Hare Airport, Chicago Midway Airport and Chicago Greater Rockford.

  • Are there any other airlines in Star Alliance that fly to Chicago?

    Unfortunately, there are no other airlines in Star Alliance that fly to Chicago.

See more FAQs

Top tips for your flights to Chicago with United Airlines

  • The cheapest flight to Chicago with United Airlines found on KAYAK in the last 2 weeks departed from Québec City and cost C$ 368.

United Airlines customer reviews

7.4
GoodBased on 11,202 verified guest reviews
8.1Crew
7.1Entertainment
7.2Comfort
6.7Food
7.7Boarding
Traveler rating:
Sort by:
R
6.8 Okay
Pros:The crew was excellent - courteous/aware/friendly. The flight, although 2 hours delayed (9;20pm scheduled departure) was pleasant and smooth. Also, the de-boarding process was surprisingly quick.
Cons:A 2 hour delay at 9:20pm at night is unfortunate yet frustrating experience, especially when we moved our flight up due to a travel warning for EWR (ironically enough, our originally scheduled flight (1922 MCO-EWR). I'm giving an overall OK (instead of good) due to the fact that there were no snacks (although I did not want anything, it didn't go unnoticed) and although there was free inflight entertainment for personal devices, I feel the passengers should have been given free internet access - in my opinion, it would have been the appropriate thing to do. In any case, this experience doesn't change my positive opinion of United.
A
4.6 Mediocre
Cons:The first contact in the airport was quite rude when informing me that I had to measure my suitcase for size. I have carried this suitcase on on every airline for over 10 years....the size got smaller and United got $25.00....not happy. There was NO free movies, no access to TV, flight pattern....nothing and it could not be turned off. ONE cookie for a coast-to-coast flight. What happened to United?
A
10.0 Wonderful
Pros:Nice smooth flight
Cons:Everything
A
10.0 Wonderful
On time departure and arrival.
A
7.0 Good
Cons:THe sits where very uncomfortable.
A
2.0 Poor
Cons:Cancelled due to Maintenance. No Communication.
B
8.3 Very good
Pros:Prompt departures, pleasant staff clean plane
A
2.0 Poor
Pros:Everything was good, thanks to all.
Cons:Thanks to crews for safe flight
A
3.3 Poor
Cons:See above.
A
10.0 Wonderful
Pros:Availability of flights out of Chicago
Cons:Availability of flights out of Chicago
Read more about United Airlines

Book Cheap flights with United Airlines to Chicago

Recent round-trip flight deals

19/5Sun
directUnited Airlines
1h 54mYYZ-ORD
25/5Sat
1 stopUnited Airlines
13h 32mORD-YYZ
C$ 339
16/6Sun
directUnited Airlines
1h 56mYYZ-ORD
22/6Sat
directUnited Airlines
1h 43mORD-YYZ
C$ 348
23/5Thu
directUnited Airlines
1h 56mYYZ-ORD
27/5Mon
directUnited Airlines
1h 48mORD-YYZ
C$ 360
5/6Wed
1 stopUnited Airlines
9h 35mYYZ-ORD
16/6Sun
directUnited Airlines
1h 48mORD-YYZ
C$ 370
13/5Mon
directUnited Airlines
1h 59mYYZ-ORD
13/5Mon
directUnited Airlines
1h 43mORD-YYZ
C$ 371
28/5Tue
directUnited Airlines
1h 57mYYZ-ORD
4/6Tue
directUnited Airlines
1h 43mORD-YYZ
C$ 380
21/6Fri
directUnited Airlines
1h 57mYYZ-ORD
22/6Sat
1 stopUnited Airlines
9h 14mORD-YYZ
C$ 381
13/5Mon
directUnited Airlines
1h 59mYYZ-ORD
13/5Mon
1 stopUnited Airlines
9h 40mORD-YYZ
C$ 385
15/8Thu
1 stopUnited Airlines
10h 13mYYZ-ORD
18/8Sun
directUnited Airlines
1h 48mORD-YYZ
C$ 388
25/5Sat
directUnited Airlines
2h 02mYYZ-ORD
27/5Mon
directUnited Airlines
1h 48mORD-YYZ
C$ 392
6/6Thu
directUnited Airlines
2h 31mYUL-ORD
10/6Mon
1 stopUnited Airlines
9h 39mORD-YUL
C$ 392
20/5Mon
directUnited Airlines
2h 46mYUL-ORD
25/5Sat
1 stopUnited Airlines
12h 44mORD-YUL
C$ 393
3/6Mon
directUnited Airlines
1h 57mYYZ-ORD
6/6Thu
directUnited Airlines
1h 45mORD-YYZ
C$ 395
13/7Sat
directUnited Airlines
1h 57mYYZ-ORD
20/7Sat
directUnited Airlines
1h 48mORD-YYZ
C$ 401
10/5Fri
directUnited Airlines
4h 13mYVR-ORD
14/5Tue
1 stopUnited Airlines
8h 20mORD-YVR
C$ 403
3/6Mon
directUnited Airlines
1h 56mYYZ-ORD
6/6Thu
1 stopUnited Airlines
6h 47mORD-YYZ
C$ 408
16/8Fri
1 stopUnited Airlines
12h 57mYYZ-ORD
19/8Mon
1 stopUnited Airlines
11h 49mORD-YYZ
C$ 410
19/5Sun
directUnited Airlines
1h 54mYYZ-ORD
25/5Sat
directUnited Airlines
1h 43mORD-YYZ
C$ 411
12/5Sun
directUnited Airlines
2h 04mYYZ-ORD
31/5Fri
directUnited Airlines
1h 48mORD-YYZ
C$ 412
16/6Sun
1 stopUnited Airlines
4h 28mYYZ-ORD
23/6Sun
directUnited Airlines
1h 48mORD-YYZ
C$ 415

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Recent one-way flight deals

21/5Tue
1 stopUnited Airlines
15h 36mYYC-ORD
C$ 188
20/5Mon
directUnited Airlines
1h 54mYYZ-ORD
C$ 206
24/9Tue
1 stopUnited Airlines
15h 33mYYC-ORD
C$ 212
6/5Mon
1 stopUnited Airlines
7h 56mYYC-ORD
C$ 214
13/5Mon
directUnited Airlines
1h 59mYYZ-ORD
C$ 217
28/5Tue
directUnited Airlines
2h 43mYUL-ORD
C$ 217
21/6Fri
directUnited Airlines
1h 56mYYZ-ORD
C$ 221
1/6Sat
directUnited Airlines
1h 57mYYZ-ORD
C$ 223
1/8Thu
directUnited Airlines
1h 56mYYZ-ORD
C$ 224
18/5Sat
1 stopUnited Airlines
8h 58mYVR-ORD
C$ 227
14/7Sun
1 stopUnited Airlines
5h 30mYYZ-ORD
C$ 228
1/6Sat
1 stopUnited Airlines
4h 37mYYZ-ORD
C$ 229
24/6Mon
1 stopUnited Airlines
5h 48mYYZ-ORD
C$ 231
13/5Mon
directUnited Airlines
1h 59mYYZ-ORD
C$ 232
16/5Thu
1 stopUnited Airlines
7h 01mYVR-ORD
C$ 240
28/6Fri
directUnited Airlines
1h 56mYYZ-ORD
C$ 246
10/7Wed
directUnited Airlines
4h 01mYVR-ORD
C$ 247
22/6Sat
1 stopUnited Airlines
14h 20mYYZ-ORD
C$ 249
9/7Tue
1 stopUnited Airlines
7h 55mYYZ-ORD
C$ 250
16/5Thu
directUnited Airlines
1h 59mYYZ-ORD
C$ 251

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Flights to Chicago - United Airlines

Return flight deals:

Chicago - Canada

Cabin classes:

C$ 987
First Class flights to Chicago
C$ 827
Business Class flights to Chicago
C$ 542
C$ 279

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