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Cheap flights from Regina to Chicago from $150

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 5/27. 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
0 bags

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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 am - 4:40 pm
YQR
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 pm - 11:20 pm
ORD
-
YQR
6h 50m
1 stop
$339WestJet
Tue, Sep 29 - Mon, Oct 5
United Airlines Logo
9:45 am - 12:44 am
YQR
-
ORD
13h 59m
1 stop
United Airlines Logo
1:30 pm - 9:30 pm
ORD
-
YQR
9h 00m
1 stop
$379United Airlines
Wed, Jun 17 - Sat, Jun 20
WestJet Logo
8:35 am - 4:40 pm
YQR
-
ORD
7h 05m
1 stop
WestJet Logo
5:30 pm - 7:45 pm
ORD
-
YQR
27h 15m
2 stops
$386WestJet
Tue, Sep 29 - Mon, Oct 5
Delta Logo
8:35 am - 4:40 pm
YQR
-
ORD
7h 05m
1 stop
Delta Logo
5:30 am - 5:20 pm
ORD
-
YQR
12h 50m
2 stops
$430Delta
Fri, Jun 5 - Sun, Jun 7
Multiple Airlines Logo
7:00 am - 4:40 pm
YQR
-
ORD
8h 40m
1 stop
Multiple Airlines Logo
9:48 pm - 5:20 pm
ORD
-
YQR
20h 32m
2 stops
$431Multiple Airlines
Mon, Jun 8 - Wed, Jun 10
Delta Logo
7:00 am - 4:40 pm
YQR
-
ORD
8h 40m
1 stop
Delta Logo
12:27 pm - 5:20 pm
ORD
-
YQR
5h 53m
1 stop
$432Delta
Mon, Jun 8 - Wed, Jun 10
Delta Logo
10:45 am - 7:31 pm
YQR
-
ORD
7h 46m
1 stop
Delta Logo
12:27 pm - 5:20 pm
ORD
-
YQR
5h 53m
1 stop
$438Delta
Sun, Jun 7 - Thu, Jun 11
Delta Logo
10:45 am - 11:57 pm
YQR
-
ORD
12h 12m
2 stops
Delta Logo
1:35 pm - 11:20 pm
ORD
-
YQR
10h 45m
2 stops
$444Delta
Tue, Sep 29 - Mon, Oct 5
United Airlines Logo
5:45 am - 1:23 pm
YQR
-
ORD
6h 38m
1 stop
United Airlines Logo
12:52 pm - 7:05 pm
ORD
-
YQR
7h 13m
1 stop
$453United Airlines
Fri, Sep 25 - Sat, Sep 26
Delta Logo
10:45 am - 9:25 pm
YQR
-
ORD
9h 40m
1 stop
Delta Logo
8:36 am - 5:20 pm
ORD
-
YQR
9h 44m
1 stop
$460Delta
Sat, Jun 20 - Sat, Jun 27

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
Aug 18
YQR6:00 amRegina
7h 55m
1 stop
ORD2:55 pmChicago O'Hare Intl
Aug 19
ORD9:50 amChicago O'Hare Intl
10h 20m
1 stop
YQR7:10 pmRegina
$472
Air Canada
Jun 5
YQR5:45 amRegina
12h 07m
2 stops
ORD6:52 pmChicago O'Hare Intl
Jun 7
ORD8:50 amChicago O'Hare Intl
11h 17m
1 stop
YQR7:07 pmRegina
$631

United Airlines flights from Regina to Chicago O'Hare Intl Airport

Our best United Airlines deals on Regina to Chicago O'Hare Intl Airport flight tickets
United Airlines
Jun 17
YQR9:45 amRegina
13h 59m
1 stop
ORD12:44 amChicago O'Hare Intl
Jun 20
ORD1:30 pmChicago O'Hare Intl
9h 00m
1 stop
YQR9:30 pmRegina
$379
United Airlines
Sep 25
YQR5:45 amRegina
6h 38m
1 stop
ORD1:23 pmChicago O'Hare Intl
Sep 26
ORD12:52 pmChicago O'Hare Intl
7h 13m
1 stop
YQR7:05 pmRegina
$453
United Airlines
Jul 19
YQR9:45 amRegina
13h 59m
1 stop
ORD12:44 amChicago O'Hare Intl
Jul 24
ORD12:55 pmChicago O'Hare Intl
7h 15m
1 stop
YQR7:10 pmRegina
$486

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 May 9, 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 - ORD

YQRORD

Regina

Tue 9/29

7:00 am-4:40 pm

1 stop8h 40m

Chicago O'Hare Intl

Mon 10/5

5:30 pm-11:20 pm

1 stop6h 50m

$339

ReginaChicago

YQR - ORD

YQRORD

Regina

Wed 6/17

9:45 am-12:44 am

1 stop13h 59m

Chicago O'Hare Intl

Sat 6/20

1:30 pm-9:30 pm

1 stop9h 00m

$379

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 9/29

8:35 am-4:40 pm

1 stop7h 05m

Chicago O'Hare Intl

Mon 10/5

5:30 pm-7:45 pm

2 stops27h 15m

$386

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 6/5

8:35 am-4:40 pm

1 stop7h 05m

Chicago O'Hare Intl

Sun 6/7

5:30 am-5:20 pm

2 stops12h 50m

$430

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 6/8

7:00 am-4:40 pm

1 stop8h 40m

Chicago O'Hare Intl

Wed 6/10

9:48 pm-5:20 pm

2 stops20h 32m

$431

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 6/8

7:00 am-4:40 pm

1 stop8h 40m

Chicago O'Hare Intl

Wed 6/10

12:27 pm-5:20 pm

1 stop5h 53m

$432
Quickest round-trip

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 6/7

10:45 am-7:31 pm

1 stop7h 46m

Chicago O'Hare Intl

Thu 6/11

12:27 pm-5:20 pm

1 stop5h 53m

$438

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 9/29

10:45 am-11:57 pm

2 stops12h 12m

Chicago O'Hare Intl

Mon 10/5

1:35 pm-11:20 pm

2 stops10h 45m

$444

ReginaChicago

YQR - ORD

YQRORD

Regina

Fri 9/25

5:45 am-1:23 pm

1 stop6h 38m

Chicago O'Hare Intl

Sat 9/26

12:52 pm-7:05 pm

1 stop7h 13m

$453

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 6/20

10:45 am-9:25 pm

1 stop9h 40m

Chicago O'Hare Intl

Sat 6/27

8:36 am-5:20 pm

1 stop9h 44m

$460

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 airline that flies from Regina to Chicago O'Hare Intl?

WestJet and United Airlines are the most popular carriers operating from Regina to Chicago O'Hare Intl

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 38m

Direct flights

None
The fastest flight from Regina to Chicago O'Hare Intl Airport takes 6h 38m
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 38m, 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
South Haven
Schaumburg
Rockford
Merrillville
Gurnee
Rosemont
Naperville
New Buffalo
Orland Park
Oak Brook
Kenosha
Joliet
Aurora
Racine
Janesville
Hammond
Evanston
Elgin
Tinley Park

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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