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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 4/16. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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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
4:25 pm - 1:35 pm
YQR
-
ORD
21h 10m1 stop
WestJet Logo
2:20 pm - 9:06 pm
ORD
-
YQR
6h 46m1 stop
$219WestJet
Thu, Feb 5 - Mon, Feb 9
United Airlines Logo
10:45 am - 11:59 pm
YQR
-
ORD
13h 14m1 stop
United Airlines Logo
7:10 am - 10:51 pm
ORD
-
YQR
15h 41m1 stop
$222United Airlines
Sat, Jan 10 - Wed, Mar 4
WestJet Logo
7:05 am - 1:35 pm
YQR
-
ORD
30h 30m2 stops
WestJet Logo
2:20 pm - 9:06 pm
ORD
-
YQR
6h 46m1 stop
$294WestJet
Thu, Feb 5 - Mon, Feb 9
WestJet Logo
6:10 pm - 1:35 pm
YQR
-
ORD
19h 25m2 stops
WestJet Logo
2:20 pm - 10:32 am
ORD
-
YQR
44h 12m2 stops
$300WestJet
Thu, Feb 5 - Mon, Feb 9
United Airlines Logo
10:45 am - 6:46 pm
YQR
-
ORD
8h 01m1 stop
United Airlines Logo
7:25 am - 10:51 pm
ORD
-
YQR
15h 26m2 stops
$347United Airlines
Sat, Jan 10 - Wed, Mar 4
United Airlines Logo
10:45 am - 6:46 pm
YQR
-
ORD
8h 01m1 stop
United Airlines Logo
1:55 pm - 10:51 pm
ORD
-
YQR
8h 56m1 stop
$361United Airlines
Thu, Feb 5 - Mon, Feb 9
Multiple Airlines Logo
7:00 am - 2:17 pm
YQR
-
ORD
31h 17m3 stops
Multiple Airlines Logo
2:20 pm - 10:32 am
ORD
-
YQR
20h 12m2 stops
$407Multiple Airlines
Thu, Feb 5 - Mon, Feb 9
United Airlines Logo
5:40 am - 8:17 pm
YQR
-
ORD
14h 37m2 stops
United Airlines Logo
1:55 pm - 10:51 pm
ORD
-
YQR
8h 56m1 stop
$420United Airlines
Mon, Jan 12 - Thu, Jan 15
Delta Logo
11:45 am - 8:40 am
YQR
-
ORD
20h 55m1 stop
Delta Logo
8:50 am - 6:20 pm
ORD
-
YQR
9h 30m1 stop
$448Delta
Mon, Jan 12 - Thu, Jan 15
WestJet Logo
7:00 am - 6:58 pm
YQR
-
ORD
11h 58m2 stops
WestJet Logo
7:10 am - 1:15 am
ORD
-
YQR
18h 05m2 stops
$453WestJet
Sat, Jan 10 - Wed, Mar 4

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
Feb 5
YQR4:25 pmRegina
21h 10m
1 stop
ORD1:35 pmChicago O'Hare Intl
Feb 9
ORD2:20 pmChicago O'Hare Intl
6h 46m
1 stop
YQR9:06 pmRegina
$219
Find similar
WestJet
Feb 5
YQR7:05 amRegina
30h 30m
2 stops
ORD1:35 pmChicago O'Hare Intl
Feb 9
ORD2:20 pmChicago O'Hare Intl
6h 46m
1 stop
YQR9:06 pmRegina
$294
Find similar
WestJet
Feb 5
YQR6:10 pmRegina
19h 25m
2 stops
ORD1:35 pmChicago O'Hare Intl
Feb 9
ORD2:20 pmChicago O'Hare Intl
44h 12m
2 stops
YQR10:32 amRegina
$300
Find similar

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
Jan 10
YQR10:45 amRegina
13h 14m
1 stop
ORD11:59 pmChicago O'Hare Intl
Mar 4
ORD7:10 amChicago O'Hare Intl
15h 41m
1 stop
YQR10:51 pmRegina
$222
Find similar
United Airlines
Jan 10
YQR10:45 amRegina
8h 01m
1 stop
ORD6:46 pmChicago O'Hare Intl
Mar 4
ORD7:25 amChicago O'Hare Intl
15h 26m
2 stops
YQR10:51 pmRegina
$347
Find similar
United Airlines
Feb 5
YQR10:45 amRegina
8h 01m
1 stop
ORD6:46 pmChicago O'Hare Intl
Feb 9
ORD1:55 pmChicago O'Hare Intl
8h 56m
1 stop
YQR10:51 pmRegina
$361
Find similar

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 December 18, 2025.
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

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 2/5

4:25 pm-1:35 pm

1 stop21h 10m

Chicago O'Hare Intl

Mon 2/9

2:20 pm-9:06 pm

1 stop6h 46m

$219

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 1/10

10:45 am-11:59 pm

1 stop13h 14m

Chicago O'Hare Intl

Wed 3/4

7:10 am-10:51 pm

1 stop15h 41m

$222

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 2/5

7:05 am-1:35 pm

2 stops30h 30m

Chicago O'Hare Intl

Mon 2/9

2:20 pm-9:06 pm

1 stop6h 46m

$294

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 2/5

6:10 pm-1:35 pm

2 stops19h 25m

Chicago O'Hare Intl

Mon 2/9

2:20 pm-10:32 am

2 stops44h 12m

$300

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 1/10

10:45 am-6:46 pm

1 stop8h 01m

Chicago O'Hare Intl

Wed 3/4

7:25 am-10:51 pm

2 stops15h 26m

$347

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 2/5

10:45 am-6:46 pm

1 stop8h 01m

Chicago O'Hare Intl

Mon 2/9

1:55 pm-10:51 pm

1 stop8h 56m

$361

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 2/5

7:00 am-2:17 pm

3 stops31h 17m

Chicago O'Hare Intl

Mon 2/9

2:20 pm-10:32 am

2 stops20h 12m

$407

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 1/12

5:40 am-8:17 pm

2 stops14h 37m

Chicago O'Hare Intl

Thu 1/15

1:55 pm-10:51 pm

1 stop8h 56m

$420

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 1/12

11:45 am-8:40 am

1 stop20h 55m

Chicago O'Hare Intl

Thu 1/15

8:50 am-6:20 pm

1 stop9h 30m

$448

ReginaChicago

YQR - ORD

YQRORD

Regina

Sat 1/10

7:00 am-6:58 pm

2 stops11h 58m

Chicago O'Hare Intl

Wed 3/4

7:10 am-1:15 am

2 stops18h 05m

$453

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 13 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 day to depart on your flight to Chicago O'Hare Intl Airport?

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Friday when prices can be found for as low as $285. This is often the case because there is less demand to fly during this day of the week. On the other hand, Thursday is the most expensive day to depart from Regina because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $590.

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

10h 26m

Direct flights

None
The fastest flight from Regina to Chicago O'Hare Intl Airport takes 10h 26m
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

  • 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 10h 26m, 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
South Haven
Rockford
Merrillville
Gurnee
Naperville
Rosemont
Kenosha
New Buffalo
Joliet
Oak Brook
Orland Park
Racine
Hammond
Janesville
Tinley Park
Aurora
Elgin
Benton Harbor

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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