ORD - YQR

$253 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 1/4. 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
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41.299.237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$295
Multiple Airlines
Mon 1/26Thu 1/29
ORD - YQR • 1 stop
Cheapest one-way
$253
Multiple Airlines
Sun 1/4
ORD - YQR • 3 stops
Top airlines
WestJet
Cheapest • from $297 (round-trip)
United Airlines
Best reviews • 7.4 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
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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, Jan 26 - Thu, Jan 29
Multiple Airlines Logo
2:20 pm - 9:08 pm
ORD
-
YQR
6h 48m1 stop
Multiple Airlines Logo
4:15 pm - 8:29 pm
YQR
-
ORD
28h 14m1 stop
$295Multiple Airlines
Fri, Mar 6 - Sun, Mar 8
WestJet Logo
2:20 pm - 12:18 am
ORD
-
YQR
9h 58m1 stop
WestJet Logo
7:20 pm - 1:35 pm
YQR
-
ORD
17h 15m1 stop
$297WestJet
Fri, Mar 6 - Sun, Mar 8
WestJet Logo
2:20 pm - 11:41 am
ORD
-
YQR
21h 21m1 stop
WestJet Logo
10:05 am - 1:35 pm
YQR
-
ORD
26h 30m2 stops
$315WestJet
Mon, Jan 26 - Thu, Jan 29
WestJet Logo
2:20 pm - 9:08 pm
ORD
-
YQR
6h 48m1 stop
WestJet Logo
6:10 pm - 1:35 pm
YQR
-
ORD
19h 25m2 stops
$316WestJet
Thu, Feb 5 - Thu, Feb 12
Multiple Airlines Logo
2:00 pm - 11:19 pm
ORD
-
YQR
9h 19m1 stop
Multiple Airlines Logo
6:10 pm - 1:35 pm
YQR
-
ORD
19h 25m2 stops
$359Multiple Airlines
Thu, Feb 5 - Thu, Feb 12
Multiple Airlines Logo
2:00 pm - 11:19 pm
ORD
-
YQR
9h 19m1 stop
Multiple Airlines Logo
2:10 pm - 1:35 pm
YQR
-
ORD
23h 25m1 stop
$362Multiple Airlines
Mon, Jan 26 - Thu, Jan 29
WestJet Logo
2:20 pm - 10:32 am
ORD
-
YQR
20h 12m2 stops
WestJet Logo
6:10 pm - 1:35 pm
YQR
-
ORD
19h 25m2 stops
$367WestJet
Fri, Jan 23 - Sun, Jan 25
Air Canada Logo
8:45 pm - 10:39 am
ORD
-
YQR
13h 54m1 stop
Air Canada Logo
5:00 am - 3:10 pm
YQR
-
ORD
10h 10m1 stop
$382Air Canada
Fri, Jan 23 - Sun, Jan 25
Air Canada Logo
8:45 pm - 10:39 am
ORD
-
YQR
13h 54m1 stop
Air Canada Logo
5:00 am - 3:10 pm
YQR
-
ORD
10h 10m1 stop
$393Air Canada
Thu, Feb 5 - Thu, Feb 12
Multiple Airlines Logo
8:43 pm - 1:15 am
ORD
-
YQR
28h 32m2 stops
Multiple Airlines Logo
6:10 pm - 1:35 pm
YQR
-
ORD
19h 25m2 stops
$461Multiple 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’s the cheapest day of the week to fly from Chicago to Regina?

The average price of all round-trip flights from Chicago O'Hare Intl Airport to Regina clicked on KAYAK for each day over the last 12 months.

If your flying dates are flexible, you should consider flying to Regina on a Wednesday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from Chicago to Regina. For your return ticket, we recommend flying on a Friday and avoiding Thursdays for the best deals.

Good to know

Low seasonJuly
Cheapest flight$253
Best time to beat the crowds with an average 47% drop in price.
Most popular time to fly and prices are also 30% 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 $253 for a one-way ticket and $295 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 9111 reviews
7.7Boarding
7.1Entertainment
6.6Food
8.1Crew
7.3Comfort
Airline reviews

I liked the snacks and the flight attendants were friendly.

8.0 ExcellentAnonymous, Dec 2025
ORD - PHX
Read more United Airlines reviews

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.

Very thoughtful flight attendant offered me water immediately since I had run to make my connection.

Seats in waiting area and on plane hard as rock. Fast internet on the flight was great! Crew was kind.

Always wish for more healthy, gluten free options. We have to bring our own.

Having a long layover, I was very appreciative of the ability to stand by for an earlier flight. Other airlines like Delta have refused this to me in the past, just to be mean (because my ticket class wasn't high enough). United went out of their way to help me get to my destination early, which I really appreciated given that it was the third leg of a 24+ hour journey for me.

Other than a way way too cold cabinets for the entire flight, all was great

One bag is incorrect and not acceptable for an international flight. The food was not just good. I won't fly with them again.

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.

Kayak was the problem! The tickets we bought did not allow for carry on or checked luggage and we ended up paying more for those services than the tickets! The paperwork Kayak provided for the receipt left the luggage policy for Westair intentionally blank. This was intentionally decietful on Kayak's part. Our additional cost was over $400.00! I will be calling customer service today asking for refunds and I will keep you informed on any review sites as I can. Keith

Leaving the same day as planned would've been better

I like the web site, prompt notifications, website checks in process, and airport check in. The flight attendants are attentive and polite. The return flight was 2 hours late and reason vine doesn't sound like an unplanned and unexpected issue (scheduled plane maintenance).

Our flight was delayed almost 3.5 hours (some of the issue seemed to be weather-related, yes) but NOTHING was offered as an conciliatory gesture for this delay. No food offering or any additional drink offering. There is no entertainment is available on any screen behind the seats. The airlines are so quick to penalize customers for slightest requests for comfort- seat changes, complicated baggage allowances, seating zones which are utterly dehumanizing (ZONE 9? after Zone 4- why? This is so clearly meant to be a message to those that do not have 'loyalty' to this airline to make a distinguishing line in the sand. There is such a lack of humanity in the way people are corralled in and spoken to. So, I don't think airlines should be all that surprised when those some dehumanizing corporate treatment is returned to them when asked. The flight on the way into Calgary was scheduled to arrived at 9:25 and we arrived at 12:45 AM. It is not okay. I would think TWICE and possibly once more before booking with them again. Their overhead bins are small and limited so they bully you into either paying for a $90 checked bag or gate check a lot of people's bags. Often on their website there is no carry-on bag allowance. Beware!

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

Information on your arrival and departure airports