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Find cheap United Airlines flights to Chicago from C$ 192

1 adult
0 bags
Sat 29/6
Sat 6/7

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Good to know

Low season

January

High season

May

Cheapest flight

C$ 192

Average price round-trip

C$ 611
Best time to beat the crowds (18% less expensive on average)
Most popular time to fly and prices are also 3% lower on average.
Flight from Calgary to Chicago O'Hare Airport
(price for this month)

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 Air Canada, Porter Airlines, Air Canada and Porter Airlines.

  • 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?

    If you want to fly with an airline in Star Alliance, Air Canada and Air Canada also fly to Chicago.

United Airlines customer reviews

7.4
GoodBased on 10,777 verified guest reviews
6.7Food
7.1Entertainment
7.7Boarding
8.1Crew
7.2Comfort
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
On time departure and arrival.
A
10.0 Wonderful
Pros:Nice smooth flight
Cons:Everything
B
5.6 Fair
Cons:More water, drinks. The food was absolutely horrible.
A
7.3 Good
Pros:Amazing crew
Cons:Tight seats, no access to actual WiFi unless you purchase a yearly or monthly plan
S
4.6 Mediocre
Pros:Ordered the Protein Box, it was ok.. crew members nice.
Cons:The Smell on the flight was unacceptable, I was sitting about a couple rows across the middle bathroom, and it smelled horrible, I had never had an experience like this on any other flight, I fly United many times a year, and this had me really uncomfortable for almost 5 hours, since the flight was delayed almost 1.5 hours while we sat onboard the aircraft at the gate, that had me miss dinner plans too in San Francisco as well. I really hope they can fix that, For the good of the passengers, felt like I was going to be nauseous all the time, and I'm really not someone that complains or takes time to review badly.
N
4.6 Mediocre
Cons:2.5 hour delay. No working bathrooms. Couldn't hear the tv and headphones that they gave out were useless.
A
2.0 Poor
Cons:Purchased tickets 4 months before this flight for a departure time of 6:05pm. Tried to check in and check baggage at 9:30am but was turned away saying I could only check in 3 hrs prior to my flight. Came back at 3:00pm to check-in and they could not find my information. An hour later they find out that they cancelled the flight and moved my departure time to 8:25am for that day. They say they emailed 3 times in May but I never got it (I'm a bit crazy about my email staying clean) so they say it might have went in to my spam folder due to they types of emails they send to customers. They only kept repeating that they notified me so there is nothing they could do. I ended up going to Air Canada to get a flight to PHX the next day. No apology, no help, no hotel for the night...Terrible experience by United. They gave me a customer relations group contact information to follow up with for complaint but since they sent me the 3 emails in May about the change, they have no liability to fix the situation.
A
2.0 Poor
Cons:Departure was delayed. No explanation. The boarding area is crowded and confusing. The plane's bins were too small for roller boards so passengers had to carry bags outdoors in snow and terrible wind, to get them loaded. The Newark airport where the plane landed was miserable! Departure from Newark was worse than landing if that could be possible! Awful!
Read more about United Airlines

Book Cheap flights with United Airlines to Chicago

Recent round-trip flight deals

19/6Wed
directUnited Airlines
1h 57mYYZ-ORD
26/6Wed
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1h 48mORD-YYZ
C$ 313
25/10Fri
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11h 23mYYC-ORD
29/10Tue
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3h 54mORD-YYC
C$ 322
26/10Sat
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5h 48mYYC-ORD
29/10Tue
1 stopUnited Airlines
9h 34mORD-YYC
C$ 323
18/6Tue
directUnited Airlines
2h 02mYYZ-ORD
23/6Sun
directUnited Airlines
1h 48mORD-YYZ
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4/7Thu
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2h 43mYUL-ORD
7/7Sun
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19/6Wed
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2h 02mYYZ-ORD
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1 stopUnited Airlines
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28/7Sun
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directUnited Airlines
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30/9Mon
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1h 56mYYZ-ORD
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1 stopUnited Airlines
11h 29mORD-YYZ
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1 stopUnited Airlines
7h 15mYYZ-ORD
23/6Sun
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1h 48mORD-YYZ
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1h 53mYYZ-ORD
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10h 30mYYZ-ORD
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directUnited Airlines
1h 48mORD-YYZ
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1 stopUnited Airlines
10h 30mYYZ-ORD
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directUnited Airlines
4h 12mYVR-ORD
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directUnited Airlines
4h 38mORD-YVR
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1 stopUnited Airlines
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directUnited Airlines
1h 56mYYZ-ORD
21/10Mon
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11h 29mORD-YYZ
C$ 375

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Recent one-way flight deals

4/6Tue
1 stopUnited Airlines
6h 30mYYC-ORD
C$ 192
3/7Wed
1 stopUnited Airlines
13h 30mYYC-ORD
C$ 193
24/6Mon
1 stopUnited Airlines
16h 34mYYC-ORD
C$ 196
7/6Fri
1 stopUnited Airlines
7h 34mYYC-ORD
C$ 197
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1 stopUnited Airlines
14h 31mYYC-ORD
C$ 198
13/6Thu
directUnited Airlines
1h 54mYYZ-ORD
C$ 200
5/7Fri
directUnited Airlines
1h 57mYYZ-ORD
C$ 201
17/6Mon
directUnited Airlines
4h 01mYVR-ORD
C$ 211
14/6Fri
directUnited Airlines
1h 57mYYZ-ORD
C$ 216
11/6Tue
directUnited Airlines
4h 12mYVR-ORD
C$ 216
2/7Tue
1 stopUnited Airlines
12h 58mYYZ-ORD
C$ 222
25/6Tue
1 stopUnited Airlines
15h 02mYYZ-ORD
C$ 223
1/7Mon
1 stopUnited Airlines
10h 13mYYZ-ORD
C$ 224
4/7Thu
directUnited Airlines
2h 43mYUL-ORD
C$ 224
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directUnited Airlines
4h 12mYVR-ORD
C$ 226
24/7Wed
1 stopUnited Airlines
5h 28mYUL-ORD
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directUnited Airlines
1h 57mYYZ-ORD
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1 stopUnited Airlines
13h 24mYVR-ORD
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1 stopUnited Airlines
12h 20mYVR-ORD
C$ 233
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1 stopUnited Airlines
12h 41mYUL-ORD
C$ 233

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Flights to Chicago - United Airlines

Return flight deals:

Chicago - Canada

Cabin classes:

C$ 1,010
First Class flights to Chicago
C$ 1,089
Business Class flights to Chicago
C$ 602
C$ 265

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