ORD - YQR

$159 Find Cheap Flights from Chicago to Regina

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Chicago to Regina departing on 4/14. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Regina

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Regina, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Chicago to Regina, as well as popular online travel agencies
Travelers love KAYAK
41 299 237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$375
WestJet
Fri 6/19Sun 6/21
ORD - YQR • 1 stop
Cheapest one-way
$159
United Airlines
Tue 4/14
ORD - YQR • 1 stop
Start a new search
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Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Chicago to Regina (ORD-YQR)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Chicago to Regina that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Chicago to Regina

Fri, Jun 19 - Sun, Jun 21
WestJet Logo
5:30 pm - 1:07 am
ORD
-
YQR
8h 37m
1 stop
WestJet Logo
11:45 am - 4:43 pm
YQR
-
ORD
27h 58m
1 stop
$375WestJet
Mon, Mar 2 - Mon, Mar 9
WestJet Logo
2:20 pm - 10:32 am
ORD
-
YQR
20h 12m
2 stops
WestJet Logo
5:10 am - 1:35 pm
YQR
-
ORD
7h 25m
1 stop
$377WestJet
Fri, Jun 19 - Sun, Jun 21
WestJet Logo
5:30 pm - 11:02 pm
ORD
-
YQR
6h 32m
1 stop
WestJet Logo
10:05 am - 4:43 pm
YQR
-
ORD
29h 38m
2 stops
$391WestJet
Wed, Mar 4 - Wed, Mar 11
Air Canada Logo
8:40 pm - 10:39 am
ORD
-
YQR
13h 59m
1 stop
Air Canada Logo
5:00 am - 1:01 pm
YQR
-
ORD
7h 01m
1 stop
$394Air Canada
Mon, Mar 2 - Mon, Mar 9
WestJet Logo
2:20 pm - 1:55 am
ORD
-
YQR
11h 35m
1 stop
WestJet Logo
5:10 am - 1:35 pm
YQR
-
ORD
7h 25m
1 stop
$401WestJet
Thu, Apr 9 - Mon, Apr 13
Air Canada Logo
8:20 pm - 9:32 am
ORD
-
YQR
14h 12m
1 stop
Air Canada Logo
5:00 am - 7:50 pm
YQR
-
ORD
13h 50m
2 stops
$403Air Canada
Fri, Jun 19 - Sun, Jun 21
WestJet Logo
5:30 pm - 9:30 am
ORD
-
YQR
17h 00m
2 stops
WestJet Logo
5:30 pm - 4:43 pm
YQR
-
ORD
22h 13m
2 stops
$411WestJet
Fri, Jun 19 - Sun, Jun 21
WestJet Logo
5:30 pm - 11:02 pm
ORD
-
YQR
6h 32m
1 stop
WestJet Logo
5:30 pm - 4:43 pm
YQR
-
ORD
22h 13m
2 stops
$423WestJet
Thu, Apr 9 - Mon, Apr 13
Air Canada Logo
12:50 pm - 9:32 am
ORD
-
YQR
21h 42m
2 stops
Air Canada Logo
5:00 am - 7:50 pm
YQR
-
ORD
13h 50m
2 stops
$441Air Canada
Fri, Jun 19 - Sun, Jun 21
WestJet Logo
5:30 pm - 9:30 am
ORD
-
YQR
17h 00m
2 stops
WestJet Logo
10:05 am - 4:43 pm
YQR
-
ORD
29h 38m
2 stops
$453WestJet
Booking Insights

KAYAK's insights & trends for Chicago to Regina flights

Get data-powered insights and trends into flights from Chicago to Regina to help you find the cheapest flights, the best time to fly and much more.

What is the most popular layover airport when flying from Chicago to Regina?

Percentage of 1-stop round-trip flights from Chicago to Regina chosen by KAYAK users via each layover airport in the last 12 months (only includes trips with the same layover airport on both legs).

Calgary (YYC) is the top choice – 34% of KAYAK users who clicked on 1-stop flights from Chicago to Regina picked an itinerary connecting there.

What is the cheapest layover airport when flying from Chicago to Regina?

Average round-trip price for 1-stop flights from Chicago to Regina clicked by KAYAK users in the last 12 months (only includes trips with the same layover airport on both legs).

Flights via Calgary (YYC) offer the most affordable fares, with an average round-trip price of $354.

Which layover airport offers the shortest total travel time from Chicago to Regina?

Shortest average total travel time for 1-stop one-way flights from Chicago to Regina via different layover airports, based on KAYAK user data from the last 12 months.

Consider flying via Minneapolis (MSP) for the shortest journey. The average one-way travel time for flights connecting there is 6h 17m.

Which layover airport has the quickest connection when flying from Chicago to Regina?

Average layover duration at different layover airports for 1-stop one-way flights from Chicago to Regina, based on KAYAK user data from the last 12 months.

If you prefer a quick connection, Denver (DEN) often has the shortest layovers from Chicago to Regina, with an average of 1h 57m.

Good to know

Cheapest flight$159
Flight from Chicago to Regina

When to book flights from Chicago to Regina

Are your dates flexible? Find out the best times to travel from Chicago to Regina based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking Chicago to Regina flights

  • What is the cheapest flight from Chicago O'Hare Intl Airport to Regina?

    In the last 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Regina was $159 for a one-way ticket and $375 for a round-trip.

  • Do I need a passport to fly between Chicago and Regina?

    A passport is required to fly from Chicago to Regina.

  • Which airports will I be using when flying from Chicago to Regina?

    On your way to Regina, you’ll fly out from Chicago O'Hare Intl. You’ll be landing at Regina.

  • Which aircraft models fly most regularly from Chicago to Regina?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Chicago to Regina?

    Star Alliance is the only airline alliance operating flights between Chicago and Regina.

  • Which is the best airline for flights from Chicago to Regina, United Airlines or WestJet?

    The two airlines most popular with KAYAK users for flights from Chicago to Regina are United Airlines and WestJet. With an average price for the route of $336 and an overall rating of 7.4, United Airlines is the most popular choice. WestJet is also a great choice for the route, with an average price of $373 and an overall rating of 7.2.

  • How does KAYAK find such low prices on flights from Chicago to Regina?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Chicago to Regina.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Chicago to Regina?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Regina from Chicago is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Chicago to Regina?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Regina with an airline and back to Chicago with another airline. Booking your flights between Chicago and YQR can sometimes prove cheaper using this method.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Chicago to Regina?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Regina from Chicago up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Chicago to Regina

 
See real verified KAYAK customer reviews for airlines flying from Chicago to Regina. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Chicago to Regina? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.4
United AirlinesOverall score based on 9174 reviews
8.1Crew
7.1Entertainment
7.7Boarding
7.3Comfort
6.6Food
Airline reviews

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

6.0 GoodPatricia, Jan 2026
ORD - LAS
Read more United Airlines reviews

They lost my luggage, so, not happy. The crew was nice but my suitcases never made it, still trying to find out what happened!

I understand weather is an issue, but making us chase our plane down at five scheduled gates across three terminals in an airport the size of O'Hare was unfair. They'd have probably been better off to leave gates as TBD until the inbound plane is in final approach instead of running us all over the place. Also, props to the consistently-unprepared ground crew in Richmond for once again leaving my lane parked short of the gate because they couldn't have a crew in place on time with 2 hours notice...

cabin crew was OK, food was OK, the trip from the US to Munich was actually pretty bad comfort wise. Noisy aircraft, lights never dimmed even in Business class (night flight) barely sufficient amenities for the price. I have millions of miles with United but TBH American is gaining ground and Delta has always been marginally better then United although on paper United has more longes and cheaper upgrades.

Essy to get on. The hostess gave very little pop, the plane was late getting in, and we are still waiting for our bags. This sucks. :/

Not United Airlines' fault. It's ORL airport's fault.

Great flight. On time boarding. Smooth flight and on time arrival at EWR. The flight crew was marvelous and there was a great selection of movies on the entertainment system. Our bags were at the carousel before we got there. Another excellent flight from United.

I liked the snacks and the flight attendants were friendly.

The movies offered were great. Staff were very pleasant and very efficient.

After a delay at the gate, C3, at Ohare on Sunday, I left my Blk ski coat on the bench at the gate, lost! Please review my lob claim, thx.

Very nice flight love the small aircraft. We had a wonderful flight attendant. Nice to see someone that really enjoys her job. Don't have her name but had a southern accent.

Flight was good, crew was excellent. No complaints at all

Delayed 3 times in a row for 4 hours total. Incrementally pushing back the flight claiming gate delays but they eventually changed the actual plane, due to technical issues. This strategy to avoid compensation to passengers is unprofessional.

Plane seating was uncomfortable, very tight fitting for someone my height, did not recline and overall un enjoyable

Everything was good except for flight delay, but it was because of the snow storm in the arrival airport.

No communication from Kayak or West Jet. Booked extra flights, flights cancelled, no one answers calls. Will be disputing charges.

The trip from LAX to Calgary was aboard a 737-700, which is more than twenty years old. Service was fine, and the food was good, but there was no inflight entertainment, and no WiFi. The flight from Calgary to Vancouver was also delayed more than an hour, due to congestion on the Calgary tarmac. And no food service, but there was in-flight WiFi which made a big difference.

Leg room is a problem the plane was dirty and there were no movies available on the app

The personal item sizer cannot take a standard backpack, and the cabin luggage sizer cannot take a standard carry-on. Designed for people from the island of Lilliput!!. and also compels people to pay additional fees to check their bags. Making money by ticking off the passengers is a very short-sighted business strategy, especially since they have a choice of carriers

my wife got very sick and we did not travel . we booked and bought the travel insurance and dot nothing but hassle and a triangle of stress in trying to make the insurance claim I called in and was told they would not give me anything in writing to say they would not refund my money back this make it impossible to file the claim I will never book with Kayak again.

We got delayed to the point of having a 20 hour layover. That is absurd. I couldn’t believe it. I’m furious.

Everything you need to know for your flight from Chicago to Regina

Information on your arrival and departure airports