ORD - YQR

$105 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 5/26. 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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Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$379
Typical prices: $970-$556
Multiple Airlines
Mon 6/22Mon 6/29
ORD - YQR • 1 stop
Cheapest one-way
$105
WestJet
Tue 5/26
ORD - YQR • 1 stop
Top airlines
Cheapest • from $428 (round-trip)
Best reviews • 7.4 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 $407 (round-trip)
Shortest trip • 6h 33m (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

Mon, Jun 22 - Mon, Jun 29
Multiple Airlines Logo
6:31 pm - 5:20 pm
ORD
-
YQR
23h 49m
1 stop
Multiple Airlines Logo
7:00 am - 10:27 am
YQR
-
ORD
26h 27m
2 stops
$379Multiple Airlines
Mon, Jun 22 - Mon, Jun 29
Multiple Airlines Logo
6:31 pm - 5:20 pm
ORD
-
YQR
23h 49m
1 stop
Multiple Airlines Logo
10:45 am - 10:27 am
YQR
-
ORD
22h 42m
1 stop
$380Multiple Airlines
Fri, Jun 19 - Tue, Jun 23
Multiple Airlines Logo
6:25 pm - 5:20 pm
ORD
-
YQR
23h 55m
1 stop
Multiple Airlines Logo
6:00 am - 12:48 am
YQR
-
ORD
17h 48m
2 stops
$410Multiple Airlines
Wed, Jun 24 - Wed, Jul 1
Multiple Airlines Logo
7:20 am - 5:20 pm
ORD
-
YQR
35h 00m
2 stops
Multiple Airlines Logo
10:45 am - 5:24 pm
YQR
-
ORD
5h 39m
1 stop
$417Multiple Airlines
Fri, Jun 19 - Sun, Jun 21
Air Canada Logo
8:40 pm - 9:05 am
ORD
-
YQR
13h 25m
1 stop
Air Canada Logo
5:45 am - 2:55 pm
YQR
-
ORD
8h 10m
1 stop
$428Air Canada
Mon, Jul 13 - Tue, Sep 15
Multiple Airlines Logo
6:31 pm - 5:20 pm
ORD
-
YQR
23h 49m
1 stop
Multiple Airlines Logo
7:00 am - 4:40 pm
YQR
-
ORD
8h 40m
1 stop
$445Multiple Airlines
Thu, Jun 4 - Mon, Jun 8
United Airlines Logo
7:09 am - 1:17 pm
ORD
-
YQR
7h 08m
1 stop
United Airlines Logo
5:45 am - 2:55 pm
YQR
-
ORD
8h 10m
1 stop
$478United Airlines
Wed, Jun 24 - Wed, Jul 1
Air Canada Logo
8:40 pm - 9:05 am
ORD
-
YQR
13h 25m
1 stop
Air Canada Logo
5:45 am - 1:22 pm
YQR
-
ORD
6h 37m
1 stop
$487Air Canada
Thu, Jun 4 - Mon, Jun 8
Air Canada Logo
7:09 am - 1:17 pm
ORD
-
YQR
7h 08m
1 stop
Air Canada Logo
5:45 am - 2:55 pm
YQR
-
ORD
8h 10m
1 stop
$489Air Canada
Mon, Jul 13 - Tue, Sep 15
Multiple Airlines Logo
9:57 pm - 5:20 pm
ORD
-
YQR
44h 23m
2 stops
Multiple Airlines Logo
8:35 am - 4:40 pm
YQR
-
ORD
7h 05m
1 stop
$498Multiple Airlines
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 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 seasonMay
Cheapest flight$105
Best time to beat the crowds with an average 48% drop in price.
Most popular time to fly and prices are also 38% 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 3 days, the lowest price for a flight from Chicago O'Hare Intl Airport to Regina was $105 for a one-way ticket and $379 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 $387 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 9677 reviews
8.1Crew
7.7Boarding
6.6Food
7.1Entertainment
7.3Comfort
Airline reviews

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

8.0 ExcellentTimothy, Apr 2026
ORD - CID
Read more United Airlines reviews

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.

The seat was comfortable. There was a lot of turbulence. If it weren't for that,it would have been okay.

Poor communication, flight was delayed for preventable reasons. I missed my connection.

The boarding timing needs to be improved. The flight was delayed again because it took way too long to board. I was already exhausted from sleeping at the airport and spending all day there due to delay from my previous flight that connected in Chicago.

Westjet was late and we missed our connecting flight with Cathay. Had to wait 8 hours. Westjet only allows 1 checked in baggage for international flights- it’s always been 2. Canada allows only 1 sandwhich bag size full off small liquids. Everything else will be tossed. Awful trip. Will never fly west jet or go to Toronto to connect flights!

No pre boarding kiosk to check in, baggage claim detected luggage didn’t leave the airport, poorly managed recovery of lost luggage, and blame lost tag from conveyor to TSA/security, very poor from TSA/security check to delivery, crucial if compensation will go thru and will likely wait for months unlike United,

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

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

Information on your arrival and departure airports