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Cheap flights from Regina to Chicago from C$ 259

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Regina to Chicago departing on 5/4. 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 Regina 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.
YQR
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 p.m. - 1:10 a.m.
ORD
-
YQR
8h 40m
1 stop
C$ 283WestJet
Sun, 31 May - Mon, 1 Jun
WestJet Logo
8:35 a.m. - 4:40 p.m.
YQR
-
ORD
7h 05m
1 stop
WestJet Logo
5:30 p.m. - 11:15 a.m.
ORD
-
YQR
18h 45m
2 stops
C$ 320WestJet
Sun, 31 May - Mon, 1 Jun
WestJet Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 p.m. - 12:50 p.m.
ORD
-
YQR
20h 20m
3 stops
C$ 663WestJet
Sun, 31 May - Mon, 1 Jun
Multiple Airlines Logo
2:10 p.m. - 10:05 a.m.
YQR
-
MDW
19h 55m
2 stops
Multiple Airlines Logo
11:00 a.m. - 12:15 a.m.
MDW
-
YQR
14h 15m
1 stop
C$ 712Multiple Airlines
Thu, 5 Mar - Mon, 9 Mar
Air Canada Logo
5:00 a.m. - 1:01 p.m.
YQR
-
ORD
7h 01m
1 stop
Air Canada Logo
8:40 p.m. - 9:39 a.m.
ORD
-
YQR
13h 59m
1 stop
C$ 715Air Canada
Thu, 19 Mar - Thu, 26 Mar
Delta Logo
11:35 a.m. - 6:40 p.m.
YQR
-
MDW
6h 05m
1 stop
Delta Logo
9:30 a.m. - 6:31 p.m.
MDW
-
YQR
10h 01m
1 stop
C$ 753Delta
Thu, 19 Mar - Thu, 26 Mar
Multiple Airlines Logo
9:40 a.m. - 1:35 p.m.
YQR
-
ORD
26h 55m
1 stop
Multiple Airlines Logo
7:31 p.m. - 12:15 a.m.
ORD
-
YQR
29h 44m
2 stops
C$ 763Multiple Airlines
Thu, 19 Mar - Thu, 26 Mar
Multiple Airlines Logo
6:10 a.m. - 1:35 p.m.
YQR
-
ORD
7h 25m
1 stop
Multiple Airlines Logo
4:18 p.m. - 12:15 a.m.
ORD
-
YQR
32h 57m
2 stops
C$ 782Multiple Airlines
Fri, 6 Mar - Tue, 10 Mar
Multiple Airlines Logo
4:25 p.m. - 10:05 a.m.
YQR
-
MDW
17h 40m
2 stops
Multiple Airlines Logo
11:00 a.m. - 12:15 a.m.
MDW
-
YQR
14h 15m
1 stop
C$ 793Multiple Airlines
Wed, 4 Mar - Mon, 9 Mar
Multiple Airlines Logo
7:00 a.m. - 10:05 a.m.
YQR
-
MDW
27h 05m
1 stop
Multiple Airlines Logo
11:00 a.m. - 12:15 a.m.
MDW
-
YQR
14h 15m
1 stop
C$ 804Multiple Airlines
Wed, 4 Mar - Mon, 9 Mar

United Airlines flights from Regina to Chicago

Our best United Airlines deals on Regina to Chicago flight tickets
United Airlines
2 Mar
YQR10:45 a.m.Regina
6h 20m
1 stop
ORD5:05 p.m.Chicago O'Hare Intl
3 Mar
ORD10:35 a.m.Chicago O'Hare Intl
12h 16m
1 stop
YQR10:51 p.m.Regina
C$ 952
United Airlines
2 Mar
YQR10:45 a.m.Regina
10h 44m
1 stop
ORD9:29 p.m.Chicago O'Hare Intl
3 Mar
ORD2:02 p.m.Chicago O'Hare Intl
8h 49m
1 stop
YQR10:51 p.m.Regina
C$ 1,056
United Airlines
2 Mar
YQR10:45 a.m.Regina
12h 07m
1 stop
ORD10:52 p.m.Chicago O'Hare Intl
3 Mar
ORD10:35 a.m.Chicago O'Hare Intl
12h 16m
1 stop
YQR10:51 p.m.Regina
C$ 1,086

Air Canada flights from Regina to Chicago

Our best Air Canada deals on Regina to Chicago flight tickets
Air Canada
19 Mar
YQR5:00 a.m.Regina
7h 01m
1 stop
ORD1:01 p.m.Chicago O'Hare Intl
26 Mar
ORD8:40 p.m.Chicago O'Hare Intl
13h 59m
1 stop
YQR9:39 a.m.Regina
C$ 715
Air Canada
6 Mar
YQR5:00 a.m.Regina
8h 01m
1 stop
ORD1:01 p.m.Chicago O'Hare Intl
9 Mar
ORD3:55 p.m.Chicago O'Hare Intl
18h 44m
1 stop
YQR9:39 a.m.Regina
C$ 873
Air Canada
18 Mar
YQR5:00 a.m.Regina
7h 01m
1 stop
ORD1:01 p.m.Chicago O'Hare Intl
22 Mar
ORD8:40 p.m.Chicago O'Hare Intl
13h 59m
1 stop
YQR9:39 a.m.Regina
C$ 891

momondo Fare Finder

 
Customize your flight search to find flights from Regina 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 20 February 2026.
Use the filters below to find and compare flights from Regina to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 31/5

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

1 stop8h 40m

Chicago O'Hare Intl

Mon 1/6

5:30 p.m.-1:10 a.m.

1 stop8h 40m

C$ 283

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 31/5

8:35 a.m.-4:40 p.m.

1 stop7h 05m

Chicago O'Hare Intl

Mon 1/6

5:30 p.m.-11:15 a.m.

2 stops18h 45m

C$ 320

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 31/5

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

1 stop8h 40m

Chicago O'Hare Intl

Mon 1/6

5:30 p.m.-12:50 p.m.

3 stops20h 20m

C$ 663

ReginaChicago

YQR - MDW

YQRMDW

Regina

Thu 5/3

2:10 p.m.-10:05 a.m.

2 stops19h 55m

Chicago Midway

Mon 9/3

11:00 a.m.-12:15 a.m.

1 stop14h 15m

C$ 712

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 19/3

5:00 a.m.-1:01 p.m.

1 stop7h 01m

Chicago O'Hare Intl

Thu 26/3

8:40 p.m.-9:39 a.m.

1 stop13h 59m

C$ 715

ReginaChicago

YQR - MDW

YQRMDW

Regina

Thu 19/3

11:35 a.m.-6:40 p.m.

1 stop6h 05m

Chicago Midway

Thu 26/3

9:30 a.m.-6:31 p.m.

1 stop10h 01m

C$ 753

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 19/3

9:40 a.m.-1:35 p.m.

1 stop26h 55m

Chicago O'Hare Intl

Thu 26/3

7:31 p.m.-12:15 a.m.

2 stops29h 44m

C$ 763

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 6/3

6:10 a.m.-1:35 p.m.

1 stop7h 25m

Chicago O'Hare Intl

Tue 10/3

4:18 p.m.-12:15 a.m.

2 stops32h 57m

C$ 782

ReginaChicago

YQR - MDW

YQRMDW

Regina

Wed 4/3

4:25 p.m.-10:05 a.m.

2 stops17h 40m

Chicago Midway

Mon 9/3

11:00 a.m.-12:15 a.m.

1 stop14h 15m

C$ 793

ReginaChicago

YQR - MDW

YQRMDW

Regina

Wed 4/3

7:00 a.m.-10:05 a.m.

1 stop27h 05m

Chicago Midway

Mon 9/3

11:00 a.m.-12:15 a.m.

1 stop14h 15m

C$ 804

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 Regina 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 April is another great option to travel to Chicago, with average flight prices from Regina averaging around C$ 379.

When to book flights from Regina to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Regina to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Regina to Chicago (YQR to CHI) flight deals and tips

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

Fastest flight time

8h 00m

Direct flights

None
The fastest flight from Regina to Chicago takes 8h 00m
There are no direct flights from Regina to Chicago. There are no popular flight routes from Regina to Chicago.
Search flight deals

  • How far is Regina to Chicago by plane?

    The distance between Regina and Chicago is about 1611.7 km. By plane, this route typically takes 8h 00m.

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

    Prices for flights from Regina Airport to Chicago were last updated today.

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

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

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Regina Airport to Chicago.

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

    The travel and health documents you'll need for your trip to Chicago may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Regina to Chicago?

Best airlines flying from Regina to Chicago

Compare and see reviews for airlines that fly from Regina to Chicago with momondo
Airline
Rating
Free Cancellation
Price
United AirlinesPriceFrom C$ 308Free CancellationRating
7.4
9,325 reviews
Search United Airlines flights

Travelling to a place near Chicago?

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

Why use momondo?

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

It is quick and easy to find Regina to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

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

Yes. momondo allows you to filter the results for Regina to Chicago flights to just show those with flexible booking policies.

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

Once all potential Regina 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 Regina to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Regina are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

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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