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Cheap flights from Regina to Chicago from C$ 194

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 28/5. 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.
United Airlines Logo
9:45 a.m. - 9:23 p.m.
YQR
-
ORD
10h 38m
1 stop
United Airlines Logo
1:43 p.m. - 9:30 p.m.
ORD
-
YQR
8h 47m
1 stop
C$ 486United Airlines
Sat, 2 May - Wed, 6 May
United Airlines Logo
9:45 a.m. - 9:23 p.m.
YQR
-
ORD
10h 38m
1 stop
United Airlines Logo
1:43 p.m. - 9:30 p.m.
ORD
-
YQR
8h 47m
1 stop
C$ 487United Airlines
Sat, 2 May - Wed, 6 May
Multiple Airlines Logo
8:35 a.m. - 4:40 p.m.
YQR
-
ORD
7h 05m
1 stop
Multiple Airlines Logo
8:06 p.m. - 5:20 p.m.
ORD
-
YQR
22h 14m
1 stop
C$ 512Multiple Airlines
Sun, 24 May - Sun, 31 May
Air Canada Logo
5:45 a.m. - 2:55 p.m.
YQR
-
ORD
8h 10m
1 stop
Air Canada Logo
8:20 p.m. - 9:05 a.m.
ORD
-
YQR
13h 45m
1 stop
C$ 523Air Canada
Mon, 25 May - Mon, 1 Jun
Air Canada Logo
5:45 a.m. - 1:25 p.m.
YQR
-
ORD
6h 40m
1 stop
Air Canada Logo
8:35 p.m. - 9:02 a.m.
ORD
-
YQR
13h 27m
1 stop
C$ 536Air Canada
Sat, 2 May - Wed, 6 May
Delta Logo
10:45 a.m. - 10:28 p.m.
YQR
-
MDW
10h 43m
2 stops
Delta Logo
6:00 a.m. - 5:20 p.m.
MDW
-
YQR
12h 20m
2 stops
C$ 554Delta
Sat, 2 May - Wed, 6 May
Delta Logo
10:45 a.m. - 6:36 p.m.
YQR
-
MDW
6h 51m
1 stop
Delta Logo
9:27 a.m. - 5:20 p.m.
MDW
-
YQR
8h 53m
2 stops
C$ 586Delta
Sat, 2 May - Wed, 6 May
WestJet Logo
10:45 a.m. - 6:05 p.m.
YQR
-
MDW
6h 20m
1 stop
WestJet Logo
9:20 a.m. - 5:20 p.m.
MDW
-
YQR
9h 00m
1 stop
C$ 1,081WestJet
Sun, 23 Aug - Fri, 28 Aug
WestJet Logo
7:00 a.m. - 6:18 p.m.
YQR
-
MDW
10h 18m
2 stops
WestJet Logo
9:49 a.m. - 5:20 p.m.
MDW
-
YQR
8h 31m
1 stop
C$ 1,089WestJet
Thu, 23 Jul - Sun, 26 Jul
Multiple Airlines Logo
2:00 p.m. - 2:35 p.m.
YQR
-
MDW
23h 35m
3 stops
Multiple Airlines Logo
10:25 a.m. - 1:10 a.m.
MDW
-
YQR
15h 45m
3 stops
C$ 1,099Multiple Airlines
Mon, 25 May - Mon, 1 Jun

United Airlines flights from Regina to Chicago

Our best United Airlines deals on Regina to Chicago flight tickets
United Airlines
2 May
YQR9:45 a.m.Regina
10h 38m
1 stop
ORD9:23 p.m.Chicago O'Hare Intl
6 May
ORD1:43 p.m.Chicago O'Hare Intl
8h 47m
1 stop
YQR9:30 p.m.Regina
C$ 486
United Airlines
2 May
YQR9:45 a.m.Regina
10h 38m
1 stop
ORD9:23 p.m.Chicago O'Hare Intl
6 May
ORD1:43 p.m.Chicago O'Hare Intl
8h 47m
1 stop
YQR9:30 p.m.Regina
C$ 487
United Airlines
5 Jun
YQR5:45 a.m.Regina
6h 40m
1 stop
ORD1:25 p.m.Chicago O'Hare Intl
7 Jun
ORD7:09 a.m.Chicago O'Hare Intl
12h 58m
1 stop
YQR7:07 p.m.Regina
C$ 626

Delta flights from Regina to Chicago

Our best Delta deals on Regina to Chicago flight tickets
Delta
2 May
YQR10:45 a.m.Regina
10h 43m
2 stops
MDW10:28 p.m.Chicago Midway
6 May
MDW6:00 a.m.Chicago Midway
12h 20m
2 stops
YQR5:20 p.m.Regina
C$ 554
Delta
3 May
YQR7:00 a.m.Regina
8h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
7 May
ORD2:00 p.m.Chicago O'Hare Intl
10h 20m
2 stops
YQR11:20 p.m.Regina
C$ 577
Delta
24 May
YQR10:45 a.m.Regina
12h 23m
2 stops
ORD12:08 a.m.Chicago O'Hare Intl
31 May
ORD8:42 a.m.Chicago O'Hare Intl
9h 38m
1 stop
YQR5:20 p.m.Regina
C$ 586

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 13 April 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

Cheapest round-trip

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 2/5

9:45 a.m.-9:23 p.m.

1 stop10h 38m

Chicago O'Hare Intl

Wed 6/5

1:43 p.m.-9:30 p.m.

1 stop8h 47m

C$ 486

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 2/5

9:45 a.m.-9:23 p.m.

1 stop10h 38m

Chicago O'Hare Intl

Wed 6/5

1:43 p.m.-9:30 p.m.

1 stop8h 47m

C$ 487

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 24/5

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

1 stop7h 05m

Chicago O'Hare Intl

Sun 31/5

8:06 p.m.-5:20 p.m.

1 stop22h 14m

C$ 512

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 25/5

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

1 stop8h 10m

Chicago O'Hare Intl

Mon 1/6

8:20 p.m.-9:05 a.m.

1 stop13h 45m

C$ 523

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 2/5

5:45 a.m.-1:25 p.m.

1 stop6h 40m

Chicago O'Hare Intl

Wed 6/5

8:35 p.m.-9:02 a.m.

1 stop13h 27m

C$ 536

ReginaChicago

YQR - MDW

YQRMDW

Regina

Sat 2/5

10:45 a.m.-10:28 p.m.

2 stops10h 43m

Chicago Midway

Wed 6/5

6:00 a.m.-5:20 p.m.

2 stops12h 20m

C$ 554

ReginaChicago

YQR - MDW

YQRMDW

Regina

Sat 2/5

10:45 a.m.-6:36 p.m.

1 stop6h 51m

Chicago Midway

Wed 6/5

9:27 a.m.-5:20 p.m.

2 stops8h 53m

C$ 586
Quickest round-trip

ReginaChicago

YQR - MDW

YQRMDW

Regina

Sun 23/8

10:45 a.m.-6:05 p.m.

1 stop6h 20m

Chicago Midway

Fri 28/8

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

1 stop9h 00m

C$ 1,081

ReginaChicago

YQR - MDW

YQRMDW

Regina

Thu 23/7

7:00 a.m.-6:18 p.m.

2 stops10h 18m

Chicago Midway

Sun 26/7

9:49 a.m.-5:20 p.m.

1 stop8h 31m

C$ 1,089

ReginaChicago

YQR - MDW

YQRMDW

Regina

Mon 25/5

2:00 p.m.-2:35 p.m.

3 stops23h 35m

Chicago Midway

Mon 1/6

10:25 a.m.-1:10 a.m.

3 stops15h 45m

C$ 1,099

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 typical price of a round-trip flight between Regina and Chicago?

What is the cheapest month to fly to Chicago?

The month of January is another great option to travel to Chicago, with average flight prices from Regina averaging around C$ 386.

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

6h 20m

Direct flights

None
The fastest flight from Regina to Chicago takes 6h 20m
There are no direct flights from Regina to Chicago. There are no popular flight routes from Regina to Chicago.
Search flight deals

Frequently asked questions about flying from Regina to Chicago

  • 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 6h 20m.

  • 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 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?

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 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