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Cheap flights from Saskatchewan to Chicago from C$ 223

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Saskatchewan to Chicago departing on 11/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

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Find the cheapest flights from Saskatchewan to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
WestJet Logo
7:00 a.m. - 4:40 p.m.
YXE
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 p.m. - 1:00 a.m.
ORD
-
YXE
8h 30m
1 stop
C$ 427WestJet
Mon, 17 Aug - Sat, 22 Aug
WestJet Logo
7:00 a.m. - 4:40 p.m.
YXE
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 p.m. - 11:10 p.m.
ORD
-
YXE
6h 40m
1 stop
C$ 455WestJet
Tue, 18 Aug - Mon, 24 Aug
WestJet Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 p.m. - 11:20 p.m.
ORD
-
YQR
6h 50m
1 stop
C$ 464WestJet
Tue, 29 Sep - Mon, 5 Oct
United Airlines Logo
9:45 a.m. - 6:51 p.m.
YQR
-
ORD
8h 06m
1 stop
United Airlines Logo
6:00 a.m. - 9:30 p.m.
ORD
-
YQR
16h 30m
1 stop
C$ 496United Airlines
Tue, 9 Jun - Tue, 16 Jun
United Airlines Logo
9:45 a.m. - 12:44 a.m.
YQR
-
ORD
13h 59m
1 stop
United Airlines Logo
1:30 p.m. - 9:30 p.m.
ORD
-
YQR
9h 00m
1 stop
C$ 519United Airlines
Wed, 17 Jun - Sat, 20 Jun
Multiple Airlines Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
Multiple Airlines Logo
9:48 p.m. - 5:20 p.m.
ORD
-
YQR
20h 32m
2 stops
C$ 529Multiple Airlines
Tue, 9 Jun - Tue, 16 Jun
Multiple Airlines Logo
3:10 p.m. - 5:29 p.m.
YXE
-
ORD
25h 19m
1 stop
Multiple Airlines Logo
6:39 p.m. - 9:35 p.m.
ORD
-
YXE
27h 56m
1 stop
C$ 547Multiple Airlines
Sun, 12 Jul - Wed, 15 Jul
Air Canada Logo
5:45 a.m. - 2:55 p.m.
YQR
-
ORD
8h 10m
1 stop
Air Canada Logo
8:45 a.m. - 7:05 p.m.
ORD
-
YQR
11h 20m
2 stops
C$ 548Air Canada
Wed, 16 Sep - Sat, 19 Sep
Delta Logo
6:00 a.m. - 6:31 p.m.
YXE
-
MDW
11h 31m
2 stops
Delta Logo
1:00 p.m. - 11:10 p.m.
MDW
-
YXE
11h 10m
2 stops
C$ 551Delta
Wed, 23 Sep - Sat, 26 Sep
Delta Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
Delta Logo
5:30 a.m. - 5:20 p.m.
ORD
-
YQR
12h 50m
2 stops
C$ 566Delta
Fri, 5 Jun - Sun, 7 Jun

Air Canada flights from Saskatchewan to Chicago

Our best Air Canada deals on Saskatchewan to Chicago flight tickets
Air Canada
16 Sep
YQR5:45 a.m.Regina
8h 10m
1 stop
ORD2:55 p.m.Chicago O'Hare Intl
19 Sep
ORD8:45 a.m.Chicago O'Hare Intl
11h 20m
2 stops
YQR7:05 p.m.Regina
C$ 548
Air Canada
16 Sep
YQR5:45 a.m.Regina
6h 38m
1 stop
ORD1:23 p.m.Chicago O'Hare Intl
19 Sep
ORD9:50 a.m.Chicago O'Hare Intl
10h 15m
1 stop
YQR7:05 p.m.Regina
C$ 595
Air Canada
23 May
YQR5:45 a.m.Regina
6h 40m
1 stop
ORD1:25 p.m.Chicago O'Hare Intl
30 Jun
ORD8:40 p.m.Chicago O'Hare Intl
13h 25m
1 stop
YQR9:05 a.m.Regina
C$ 610

WestJet flights from Saskatchewan to Chicago

Our best WestJet deals on Saskatchewan to Chicago flight tickets
WestJet
17 Aug
YXE7:00 a.m.Saskatoon
8h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
22 Aug
ORD5:30 p.m.Chicago O'Hare Intl
8h 30m
1 stop
YXE1:00 a.m.Saskatoon
C$ 427
WestJet
17 Aug
YXE7:00 a.m.Saskatoon
8h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
22 Aug
ORD5:30 p.m.Chicago O'Hare Intl
6h 40m
1 stop
YXE11:10 p.m.Saskatoon
C$ 449
WestJet
18 Aug
YXE7:00 a.m.Saskatoon
8h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
24 Aug
ORD5:30 p.m.Chicago O'Hare Intl
6h 40m
1 stop
YXE11:10 p.m.Saskatoon
C$ 455

momondo Fare Finder

 
Customize your flight search to find flights from Saskatchewan to Chicago that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 96,600 searches. Data last updated 14 May 2026.
Use the filters below to find and compare flights from Saskatchewan to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Mon 17/8

7:00 a.m.-4:40 p.m.

1 stop8h 40m

Chicago O'Hare Intl

Sat 22/8

5:30 p.m.-1:00 a.m.

1 stop8h 30m

C$ 427
Quickest round-trip

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Tue 18/8

7:00 a.m.-4:40 p.m.

1 stop8h 40m

Chicago O'Hare Intl

Mon 24/8

5:30 p.m.-11:10 p.m.

1 stop6h 40m

C$ 455

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 29/9

7:00 a.m.-4:40 p.m.

1 stop8h 40m

Chicago O'Hare Intl

Mon 5/10

5:30 p.m.-11:20 p.m.

1 stop6h 50m

C$ 464

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 9/6

9:45 a.m.-6:51 p.m.

1 stop8h 06m

Chicago O'Hare Intl

Tue 16/6

6:00 a.m.-9:30 p.m.

1 stop16h 30m

C$ 496

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 17/6

9:45 a.m.-12:44 a.m.

1 stop13h 59m

Chicago O'Hare Intl

Sat 20/6

1:30 p.m.-9:30 p.m.

1 stop9h 00m

C$ 519

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 9/6

7:00 a.m.-4:40 p.m.

1 stop8h 40m

Chicago O'Hare Intl

Tue 16/6

9:48 p.m.-5:20 p.m.

2 stops20h 32m

C$ 529

SaskatoonChicago

YXE - ORD

YXEORD

Saskatoon

Sun 12/7

3:10 p.m.-5:29 p.m.

1 stop25h 19m

Chicago O'Hare Intl

Wed 15/7

6:39 p.m.-9:35 p.m.

1 stop27h 56m

C$ 547

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 16/9

5:45 a.m.-2:55 p.m.

1 stop8h 10m

Chicago O'Hare Intl

Sat 19/9

8:45 a.m.-7:05 p.m.

2 stops11h 20m

C$ 548

SaskatoonChicago

YXE - MDW

YXEMDW

Saskatoon

Wed 23/9

6:00 a.m.-6:31 p.m.

2 stops11h 31m

Chicago Midway

Sat 26/9

1:00 p.m.-11:10 p.m.

2 stops11h 10m

C$ 551

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 5/6

7:00 a.m.-4:40 p.m.

1 stop8h 40m

Chicago O'Hare Intl

Sun 7/6

5:30 a.m.-5:20 p.m.

2 stops12h 50m

C$ 566

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Saskatchewan to Chicago

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago?

The month of December is another great option to travel to Chicago, with average flight prices from Saskatchewan averaging around C$ 174.

Can stopping save me money on Saskatchewan to Chicago flights?

You could potentially save up to 23% on your flight if you consider stops on a Saskatchewan to Chicago flight.

Cheap Saskatchewan to Chicago flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Saskatchewan to Chicago

Fastest flight time

5h 14m

Direct flights

None
The fastest flight from Saskatchewan to Chicago takes 5h 14m
There are no direct flights from Saskatchewan to Chicago. There are no popular flight routes from Saskatchewan to Chicago.
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Frequently asked questions about flying from Saskatchewan to Chicago

  • When did momondo last update prices for flights from Saskatchewan to Chicago?

    Prices for flights from Saskatchewan to Chicago were last updated today.

  • How many operators does momondo search for flights from Saskatchewan to Chicago?

  • How old do you have to be to fly from Saskatchewan to Chicago?

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Saskatchewan to Chicago.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents required for your trip to Chicago can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Saskatchewan to Chicago

Compare and see reviews for airlines that fly from Saskatchewan to Chicago with momondo
Airline
Rating
Free Cancellation
Price
WestJetPriceFrom C$ 173Free CancellationRating
7.2
3,335 reviews
Search WestJet flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
Hammond
Munster

Why use momondo?

Why should I use momondo to find a flight deal from Saskatchewan to Chicago?

momondo collates all your flight options in one place and lets you filter them to find the perfect flight from Saskatchewan to Chicago. momondo saves you time and could save you money on your trip.

Can I find flights from Saskatchewan to Chicago with flexible booking policies on momondo?

Flights from Saskatchewan to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Saskatchewan to Chicago?

Once all potential Saskatchewan to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Saskatchewan to Chicago right now. Can momondo alert me if prices change?

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Saskatchewan and alert you when they change.

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport