ORD - YQR

$202 Find Cheap Flights from Chicago to Regina - Compare and Save

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 7/2. 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
$439
WestJet
Wed 9/2Tue 9/8
ORD - YQR • 1 stop
Cheapest one-way
$202
WestJet
Thu 7/2
ORD - YQR • 1 stop
Top airlines
Cheapest • from $439 (round-trip)
Best reviews • 7.8 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Chicago and Regina. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $505 (round-trip)
Shortest trip • 6h 27m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 100% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Regina!
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

Wed, Sep 2 - Tue, Sep 8
WestJet Logo
5:30 pm - 1:10 am
ORD
-
YQR
8h 40m
1 stop
WestJet Logo
6:00 am - 4:40 pm
YQR
-
ORD
9h 40m
1 stop
$439WestJet
Thu, Nov 19 - Mon, Nov 23
Air Canada Logo
8:00 am - 11:19 pm
ORD
-
YQR
15h 19m
1 stop
Air Canada Logo
6:00 am - 2:56 pm
YQR
-
ORD
8h 56m
1 stop
$444Air Canada
Sun, Oct 25 - Thu, Oct 29
WestJet Logo
2:20 pm - 10:45 am
ORD
-
YQR
21h 25m
1 stop
WestJet Logo
5:10 am - 1:35 pm
YQR
-
ORD
7h 25m
1 stop
$445WestJet
Sun, Oct 25 - Thu, Oct 29
WestJet Logo
2:20 pm - 10:45 am
ORD
-
YQR
21h 25m
1 stop
WestJet Logo
5:10 am - 1:35 pm
YQR
-
ORD
7h 25m
1 stop
$446WestJet
Sun, Oct 25 - Thu, Oct 29
WestJet Logo
2:20 pm - 9:30 am
ORD
-
YQR
20h 10m
2 stops
WestJet Logo
5:10 am - 1:35 pm
YQR
-
ORD
7h 25m
1 stop
$453WestJet
Sun, Oct 25 - Thu, Oct 29
WestJet Logo
2:20 pm - 9:30 am
ORD
-
YQR
20h 10m
2 stops
WestJet Logo
5:10 pm - 1:35 pm
YQR
-
ORD
19h 25m
2 stops
$468WestJet
Thu, Nov 19 - Mon, Nov 23
Delta Logo
12:15 pm - 7:21 pm
ORD
-
YQR
7h 06m
1 stop
Delta Logo
10:40 am - 9:34 pm
YQR
-
ORD
10h 54m
2 stops
$503Delta
Thu, Jul 16 - Thu, Jul 23
United Airlines Logo
6:00 am - 9:30 pm
ORD
-
YQR
16h 30m
1 stop
United Airlines Logo
9:45 am - 12:44 am
YQR
-
ORD
13h 59m
1 stop
$504United Airlines
Fri, Jul 3 - Mon, Jul 20
United Airlines Logo
4:12 pm - 9:30 pm
ORD
-
YQR
6h 18m
1 stop
United Airlines Logo
9:45 am - 11:19 pm
YQR
-
ORD
12h 34m
1 stop
$505United Airlines
Thu, Nov 19 - Mon, Nov 23
Delta Logo
8:55 am - 7:21 pm
ORD
-
YQR
10h 26m
2 stops
Delta Logo
10:40 am - 9:34 pm
YQR
-
ORD
10h 54m
2 stops
$513Delta
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.

How much is a round-trip flight from Chicago O'Hare Intl Airport to Regina?

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Chicago O'Hare Intl Airport to Regina departing in September.

What is the cheapest month to fly from Chicago O'Hare Intl Airport to Regina?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Chicago O'Hare Intl Airport to Regina, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Chicago O'Hare Intl Airport to Regina is January, where tickets cost $0 (return) on average. On the other hand, the most expensive months are February and March, where the average cost of round-trip tickets is $1,145 and $863 respectively.

Good to know

Low seasonOctober
Cheapest flight$202
Best time to beat the crowds with an average 48% drop in price.
Most popular time to fly and prices are also 6% lower on average.
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 5 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Regina was $202 for a one-way ticket and $439 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?

    SkyTeam, and Star Alliance are the airline alliances operating flights between Chicago and Regina, with SkyTeam being the most commonly used for this route.

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

    The two airlines most popular with KAYAK users for flights from Chicago to Regina are Delta and United Airlines. With an average price for the route of $609 and an overall rating of 7.8, Delta is the most popular choice. United Airlines is also a great choice for the route, with an average price of $709 and an overall rating of 7.4.

  • 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.
7.8
DeltaOverall score based on 8423 reviews
7.8Comfort
7.2Food
8.1Boarding
8.5Crew
7.8Entertainment
Airline reviews

The flights are constantly late anymore, and they won't even give you a glass of water on the plane. For years, they were able to do a service on this flight from Atlanta to Knoxville and Knoxville Atlanta now they say it's too short of a flight. You can't even get a quick drink of water.

4.0 OkayKelli, Jun 2026
ATL - TYS
Read more Delta reviews

The flights are constantly late anymore, and they won't even give you a glass of water on the plane. For years, they were able to do a service on this flight from Atlanta to Knoxville and Knoxville Atlanta now they say it's too short of a flight. You can't even get a quick drink of water.

Flight got canceled 4 times, missed my connecting flight due to delays, have to wait to go home tomorrow

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Great experience nice pilot very soft and easy landing and take off

We sat on the runway for over an hour before departure. That was unwelcome.

Horrible. Faucet in sink not working, wifi not working. Didn’t bring food or snacks

Flight was delayed before take off and at landing. Baggage took 20 minutes. Flight crew would not serve full soft drink and had to ask multiple times before receiving water.

From checking to boarding, it was a seamless experience. The service agents were so helpful. The flight crew was so pleasant.

Gate agent showed up 20 minutes before boarding and was not at all friendly. Had to take this flight due to the one on the day before being cancelled and any later options were already full with long standby lists. Despite having paid for Delta Comfort seats, Delta did not allow me (or anyone) to choose their seat. The agent assigned them for everyone just prior to boarding. Self seat selection was allowed on the original flight. Flight staff was great - very friendly.

Flight attendants were great. Cheerful, upbeat and friendly. Jet, in particular, was fantastic.

Horrible! Several delays and then was cancelled! I spent over 24 hours in the airport and was unable to get a hotel or food voucher.

Smooth travel. Immediate update prior flight delay so I can arrange myself properly without too rush.

Boarded early; and arrived home 40 mins early. After a long flight, it’s nice to be back home early. These flights have no amenities; no snacks. So need to bring your own

A long delay. Don't travel late in the day.

Super friendly with lots of drink options an entertainment. Friendly crew.

The crew was great. Very friendly and responsive. The plane was old, small and tight. We ran out of overhead space and I had to check. Middle seat was particularly tight.

Several missed and almost missed connections. It felt like everything was being patched together last minute without enough resources and it ended up being an extremely stressful experience that basically ruined our weekend on the west coast. What a waste.

Putting people that close to the bathroom, where you have to look into the bathroom as people are exiting and entering was not great and the smell was also not great. I know the airlines are desperate for more chairs, but that seat is a crime.

Crew was friendly. Seats are too narrow, particularly when a big person is in the adjacent seat, but I understand this is due to smaller planes usually flight into Lincoln. I have experienced several flight delays going out and coming into Lincoln airport, I say maybe 50% or higher of the flights I've taken out of this airport have been delayed.

Great flight. Boarded efficiently. Arrived early at CLT. There was no in flight entertainment on this aircraft. Great crew.

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

Information on your arrival and departure airports