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Cheap flights from Regina to Chicago from $201

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 10/10. 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
1 adult, Economy, 0 bags

Find the cheapest flights from Regina to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Air Canada Logo
5:45 am - 2:55 pmYQR  Regina-ORD Chicago O'Hare Intl
8h 10m1 stop Toronto Pearson Intl
Air Canada Logo
9:55 am - 7:05 pmORD  Chicago O'Hare Intl-YQR Regina
10h 10m1 stop Toronto Pearson Intl
$375Air Canada
Thu, Sep 17 - Thu, Sep 24
WestJet Logo
2:00 pm - 4:40 pmYQR  Regina-ORD Chicago O'Hare Intl
25h 40m1 stop Calgary
WestJet Logo
5:30 pm - 11:20 pmORD  Chicago O'Hare Intl-YQR Regina
6h 50m1 stop Calgary
$385WestJet
Thu, Oct 1 - Mon, Oct 5
Air Canada Logo
12:40 pm - 7:48 pmYQR  Regina-ORD Chicago O'Hare Intl
6h 08m1 stop Toronto Pearson Intl
Air Canada Logo
8:40 pm - 9:10 amORD  Chicago O'Hare Intl-YQR Regina
13h 30m1 stop Toronto Pearson Intl
$391Air Canada
Mon, Oct 12 - Tue, Oct 13
Multiple Airlines Logo
10:45 am - 6:43 pmYQR  Regina-ORD Chicago O'Hare Intl
6h 58m1 stop Minneapolis St Paul
Multiple Airlines Logo
5:30 pm - 1:10 amORD  Chicago O'Hare Intl-YQR Regina
8h 40m1 stop Calgary
$398Multiple Airlines
Thu, Oct 8 - Sun, Oct 11
WestJet Logo
8:35 am - 4:40 pmYQR  Regina-ORD Chicago O'Hare Intl
7h 05m1 stop Calgary
WestJet Logo
5:30 pm - 11:20 pmORD  Chicago O'Hare Intl-YQR Regina
6h 50m1 stop Calgary
$416WestJet
Thu, Aug 27 - Fri, Sep 11
WestJet Logo
11:50 am - 4:40 pmYQR  Regina-ORD Chicago O'Hare Intl
27h 50m2 stops Edmonton Calgary
WestJet Logo
5:30 pm - 11:20 pmORD  Chicago O'Hare Intl-YQR Regina
6h 50m1 stop Calgary
$417WestJet
Thu, Aug 27 - Fri, Sep 11
Multiple Airlines Logo
10:45 am - 7:35 pmYQR  Regina-ORD Chicago O'Hare Intl
31h 50m2 stops Minneapolis St Paul Dallas/Fort Worth
Multiple Airlines Logo
5:30 pm - 1:10 amORD  Chicago O'Hare Intl-YQR Regina
8h 40m1 stop Calgary
$419Multiple Airlines
Thu, Sep 17 - Thu, Sep 24
WestJet Logo
11:50 am - 4:40 pmYQR  Regina-ORD Chicago O'Hare Intl
27h 50m2 stops Edmonton Calgary
WestJet Logo
5:30 pm - 1:10 amORD  Chicago O'Hare Intl-YQR Regina
8h 40m1 stop Calgary
$422WestJet
Tue, Aug 25 - Fri, Aug 28
Multiple Airlines Logo
10:45 am - 6:43 pmYQR  Regina-ORD Chicago O'Hare Intl
6h 58m1 stop Minneapolis St Paul
Multiple Airlines Logo
6:05 am - 5:20 pmORD  Chicago O'Hare Intl-YQR Regina
36h 15m2 stops Dallas/Fort Worth Minneapolis St Paul
$423Multiple Airlines
Thu, Oct 8 - Sun, Oct 11
WestJet Logo
4:15 pm - 4:40 pmYQR  Regina-ORD Chicago O'Hare Intl
23h 25m1 stop Calgary
WestJet Logo
5:30 pm - 1:10 amORD  Chicago O'Hare Intl-YQR Regina
8h 40m1 stop Calgary
$427WestJet
Tue, Aug 25 - Fri, Aug 28

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Air Canada flights from Regina to Chicago O'Hare Intl Airport

Our best Air Canada deals on Regina to Chicago O'Hare Intl Airport flight tickets
Air Canada
Sep 17
YQR5:45 amRegina
8h 10m
1 stop
ORD2:55 pmChicago O'Hare Intl
Sep 24
ORD9:55 amChicago O'Hare Intl
10h 10m
1 stop
YQR7:05 pmRegina
$375
Air Canada
Oct 12
YQR12:40 pmRegina
6h 08m
1 stop
ORD7:48 pmChicago O'Hare Intl
Oct 13
ORD8:40 pmChicago O'Hare Intl
13h 30m
1 stop
YQR9:10 amRegina
$391
Air Canada
Sep 8
YQR5:45 amRegina
8h 10m
1 stop
ORD2:55 pmChicago O'Hare Intl
Sep 11
ORD8:40 pmChicago O'Hare Intl
13h 20m
1 stop
YQR9:00 amRegina
$457

WestJet flights from Regina to Chicago O'Hare Intl Airport

Our best WestJet deals on Regina to Chicago O'Hare Intl Airport flight tickets
WestJet
Oct 1
YQR2:00 pmRegina
25h 40m
1 stop
ORD4:40 pmChicago O'Hare Intl
Oct 5
ORD5:30 pmChicago O'Hare Intl
6h 50m
1 stop
YQR11:20 pmRegina
$385
WestJet
Aug 27
YQR8:35 amRegina
7h 05m
1 stop
ORD4:40 pmChicago O'Hare Intl
Sep 11
ORD5:30 pmChicago O'Hare Intl
6h 50m
1 stop
YQR11:20 pmRegina
$416
WestJet
Aug 27
YQR11:50 amRegina
27h 50m
2 stops
ORD4:40 pmChicago O'Hare Intl
Sep 11
ORD5:30 pmChicago O'Hare Intl
6h 50m
1 stop
YQR11:20 pmRegina
$417

momondo Fare Finder

 
Customize your flight search to find flights from Regina to Chicago O'Hare Intl Airport 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 832,500 searches. Data last updated August 8, 2026.
Use the filters below to find and compare flights from Regina to Chicago O'Hare Intl Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 9/17

5:45 am-2:55 pm

1 stop8h 10m

Chicago O'Hare Intl

Thu 9/24

9:55 am-7:05 pm

1 stop10h 10m

$375

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 10/1

2:00 pm-4:40 pm

1 stop25h 40m

Chicago O'Hare Intl

Mon 10/5

5:30 pm-11:20 pm

1 stop6h 50m

$385

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Mon 10/12

12:40 pm-7:48 pm

1 stop6h 08m

Chicago O'Hare Intl

Tue 10/13

8:40 pm-9:10 am

1 stop13h 30m

$391

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 10/8

10:45 am-6:43 pm

1 stop6h 58m

Chicago O'Hare Intl

Sun 10/11

5:30 pm-1:10 am

1 stop8h 40m

$398
Quickest round-trip

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 8/27

8:35 am-4:40 pm

1 stop7h 05m

Chicago O'Hare Intl

Fri 9/11

5:30 pm-11:20 pm

1 stop6h 50m

$416

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 8/27

11:50 am-4:40 pm

2 stops27h 50m

Chicago O'Hare Intl

Fri 9/11

5:30 pm-11:20 pm

1 stop6h 50m

$417

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 9/17

10:45 am-7:35 pm

2 stops31h 50m

Chicago O'Hare Intl

Thu 9/24

5:30 pm-1:10 am

1 stop8h 40m

$419

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 8/25

11:50 am-4:40 pm

2 stops27h 50m

Chicago O'Hare Intl

Fri 8/28

5:30 pm-1:10 am

1 stop8h 40m

$422

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Thu 10/8

10:45 am-6:43 pm

1 stop6h 58m

Chicago O'Hare Intl

Sun 10/11

6:05 am-5:20 pm

2 stops36h 15m

$423

ReginaChicago

YQR Regina - ORD Chicago O'Hare Intl

YQRORD

Regina

Tue 8/25

4:15 pm-4:40 pm

1 stop23h 25m

Chicago O'Hare Intl

Fri 8/28

5:30 pm-1:10 am

1 stop8h 40m

$427

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 O'Hare Intl Airport

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 O'Hare Intl Airport?

The month of March is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Regina averaging around $364.

Can stopping save me money on Regina to Chicago O'Hare Intl Airport flights?

You could potentially save up to 30% on your flight if you consider stops on a Regina to Chicago O'Hare Intl Airport flight.

When to book flights from Regina to Chicago O'Hare Intl Airport

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

Cheap Regina to Chicago O'Hare Intl Airport (YQR to ORD) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Regina to Chicago O'Hare Intl Airport

Fastest flight time

6h 08m

Direct flights

None
The fastest flight from Regina to Chicago O'Hare Intl Airport takes 6h 08m
There are no direct flights from Regina to Chicago O'Hare Intl Airport. There are no popular flight routes from Regina to Chicago O'Hare Intl Airport.
Search flight deals

Frequently asked questions about flying from Regina to Chicago O'Hare Intl Airport

  • How far is Regina to Chicago O'Hare Intl by plane?

    Regina and Chicago O'Hare Intl are 986.1 mi apart from one another. Flights usually cover this in 6h 08m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Regina Airport to Chicago O'Hare Intl Airport?

    Prices for flights from Regina Airport to Chicago O'Hare Intl Airport were last updated today.

  • How old do you have to be to fly from Regina Airport to Chicago O'Hare Intl Airport?

    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 O'Hare Intl Airport.

  • What documentation or ID do you need to fly to Chicago O'Hare Intl Airport?

    The travel and health documents you'll need for your trip to Chicago O'Hare Intl Airport 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 O'Hare Intl Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Lake Geneva
Schaumburg
Merrillville
Rockford
South Haven
Gurnee
Rosemont
Oak Brook
Orland Park
Naperville
Joliet
New Buffalo
Kenosha
Hammond
Racine
Aurora
Janesville
Elgin
South Holland
Evanston

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?

momondo does allow users to show only those flights to Chicago from Regina which offer a flexible booking policy as well as other useful filters and features.

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

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Regina to Chicago.

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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