CHI

Find cheap United Airlines flights to Chicago from C$ 156

1 adult
1 adult, Economy, 0 bags

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Flight Deals

Cheap United Airlines Flight Deals to Chicago

 
Here are some of the best deals found on KAYAK recently from United Airlines to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip United Airlines flight deals to Chicago

Sat, 28 Mar - Sat, 4 Apr
United Airlines Logo
6:00 a.m. - 8:00 a.m.
YUL
-
ORD
3h 00mdirect
United Airlines Logo
6:01 p.m. - 9:26 p.m.
ORD
-
YUL
2h 25mdirect
C$ 241United Airlines
Sat, 28 Mar - Sat, 4 Apr
United Airlines Logo
6:00 a.m. - 8:00 a.m.
YUL
-
ORD
3h 00mdirect
United Airlines Logo
7:00 a.m. - 1:09 p.m.
ORD
-
YUL
5h 09m
1 stop
C$ 254United Airlines
Mon, 4 May - Sat, 9 May
United Airlines Logo
6:35 p.m. - 11:44 p.m.
YUL
-
ORD
6h 09m
1 stop
United Airlines Logo
6:03 p.m. - 9:26 p.m.
ORD
-
YUL
2h 23mdirect
C$ 260United Airlines
Thu, 2 Apr - Sun, 5 Apr
United Airlines Logo
10:15 a.m. - 11:18 a.m.
YYZ
-
ORD
2h 03mdirect
United Airlines Logo
10:52 a.m. - 1:42 p.m.
ORD
-
YYZ
1h 50mdirect
C$ 272United Airlines
Fri, 1 May - Mon, 4 May
United Airlines Logo
6:35 p.m. - 7:26 a.m.
YUL
-
ORD
13h 51m
1 stop
United Airlines Logo
11:00 a.m. - 12:13 a.m.
ORD
-
YUL
12h 13m
1 stop
C$ 273United Airlines
Thu, 9 Apr - Mon, 13 Apr
United Airlines Logo
11:23 a.m. - 4:04 p.m.
YUL
-
ORD
5h 41m
1 stop
United Airlines Logo
4:20 p.m. - 12:13 a.m.
ORD
-
YUL
6h 53m
1 stop
C$ 274United Airlines
Fri, 22 May - Mon, 25 May
United Airlines Logo
9:45 a.m. - 11:20 a.m.
YUL
-
ORD
2h 35mdirect
United Airlines Logo
6:12 p.m. - 9:34 p.m.
ORD
-
YUL
2h 22mdirect
C$ 280United Airlines
Thu, 30 Apr - Mon, 4 May
United Airlines Logo
9:45 a.m. - 11:28 a.m.
YUL
-
ORD
2h 43mdirect
United Airlines Logo
11:15 a.m. - 7:45 p.m.
ORD
-
YUL
7h 30m
1 stop
C$ 281United Airlines
Thu, 30 Apr - Fri, 1 May
United Airlines Logo
9:45 a.m. - 11:28 a.m.
YUL
-
ORD
2h 43mdirect
United Airlines Logo
11:00 a.m. - 12:13 a.m.
ORD
-
YUL
12h 13m
1 stop
C$ 283United Airlines
Tue, 10 Mar - Sun, 15 Mar
United Airlines Logo
9:00 p.m. - 10:04 p.m.
YYZ
-
ORD
2h 04mdirect
United Airlines Logo
7:10 a.m. - 9:58 a.m.
ORD
-
YYZ
1h 48mdirect
C$ 284United Airlines
Useful Info

Good to know

Low seasonJanuary
Cheapest flightC$ 156
Average price round-tripC$ 690
Good deal round-tripC$ 587
Best time to beat the crowds but there is an average 10% increase in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from Montreal 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

  • Is United Airlines cheaper than other airlines flying to Chicago?

    With an average return price of C$ 690, United Airlines is cheaper than WestJet and Air Canada when it comes to flights to Chicago. However, the cheapest airline flying to Chicago is American Airlines, with an average return price of C$ 667.

  • Which other airlines fly to Chicago?

    Along with United Airlines, you can also fly to Chicago with American Airlines, Porter Airlines, Air Canada and WestJet.

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

    On average, United Airlines flights to Chicago cost C$ 690 for a round-trip.

  • 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?

    The only other Star Alliance airline flying to Chicago is Air Canada.

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 Vancouver Intl Airport and cost C$ 338.
  • If you’re intending to fly with United Airlines, book your flight to Chicago at least 1 week before departure to ensure a below-average price.
  • High season for flights to Chicago with United Airlines is August and prices are highest at this time. The cheapest month to fly is January.

United Airlines customer reviews

7.4
Good9,283 verified ratings
7.1Entertainment
7.3Comfort
6.6Food
8.1Crew
7.7Boarding
Traveler rating:
Sort by:
M
10.0 Wonderful
From pre boarding to flight attendant, crew and baggage handler, excellent. Didn’t lost my luggage like West jet.
A
2.0 Poor
Very disappointing given gate agent behavior. Filed a formal complaint with United.
I
6.0 Okay
Do not like the size of the overhead bin. I think staff should monitor the size of suitcases that are being carried on by passengers to ensure they meet the size requirement.
D
8.0 Very good
Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.
D
2.0 Poor
Flight delayed. WiFi connectivity very poor if not existant. Last minute arrival forced me to run to catch my connection.
A
8.0 Very good
Good. Did not feel like a 12 hour flight
D
10.0 Wonderful
Great experience flights arrived earlier than expected.
D
10.0 Wonderful
Both of my flights arrived early and check in process was smooth
A
2.0 Poor
Terrible. No customer service, no food, no drinks on a 6 hour premier economy booking.
A
2.0 Poor
worst customer service I've ever experienced
Read more about United Airlines

Everything you need to know for your flight to Chicago

Other airlines flying to Chicago

Flights from the other most popular airlines that fly to Chicago according to KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.
WestJet flights to Chicago
American Airlines flights to Chicago
Air Canada flights to Chicago
Porter Airlines flights to Chicago