Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Regina to Chicago from C$ 151

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 23/10. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names, great deals

Big names, great deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Early arrival? Instantly customize your results

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Regina to Chicago

Cheap round-trip flights

United Airlines Logo
9:45 a.m. - 10:39 p.m.YQR-ORD
11h 54m1 stop
United Airlines Logo
2:53 p.m. - 9:36 p.m.ORD-YQR
7h 43m1 stop
C$ 296United Airlines
Find Deal
Mon, 20 Oct - Fri, 24 Oct
Multiple Airlines Logo
10:15 a.m. - 6:39 p.m.YQR-ORD
7h 24m1 stop
Multiple Airlines Logo
5:30 p.m. - 5:01 p.m.ORD-YQR
24h 31m2 stops
C$ 356Multiple Airlines
Find Deal
Mon, 20 Oct - Fri, 24 Oct
WestJet Logo
5:30 p.m. - 4:43 p.m.YQR-ORD
46h 13m2 stops
WestJet Logo
5:30 p.m. - 11:01 p.m.ORD-YQR
6h 31m1 stop
C$ 363WestJet
Find Deal
Tue, 21 Oct - Fri, 24 Oct
WestJet Logo
5:30 p.m. - 4:43 p.m.YQR-ORD
46h 13m2 stops
WestJet Logo
5:30 p.m. - 5:01 p.m.ORD-YQR
24h 31m2 stops
C$ 398WestJet
Find Deal
Tue, 21 Oct - Fri, 24 Oct
Air Canada Logo
2:25 p.m. - 8:00 a.m.YQR-ORD
16h 35m2 stops
Air Canada Logo
8:40 a.m. - 6:13 p.m.ORD-YQR
10h 33m2 stops
C$ 923Air Canada
Find Deal
Mon, 20 Oct - Fri, 24 Oct

WestJet flights from Regina to Chicago

Our best WestJet deals on Regina to Chicago flight tickets
WestJet
21 Oct
YQR5:30 p.m.Regina
46h 13m
2 stops
ORD4:43 p.m.Chicago O'Hare Intl
24 Oct
ORD5:30 p.m.Chicago O'Hare Intl
6h 31m
1 stop
YQR11:01 p.m.Regina
C$ 363
Find similar
WestJet
21 Oct
YQR5:30 p.m.Regina
46h 13m
2 stops
ORD4:43 p.m.Chicago O'Hare Intl
24 Oct
ORD5:30 p.m.Chicago O'Hare Intl
24h 31m
2 stops
YQR5:01 p.m.Regina
C$ 398
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Regina to Chicago 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 96,600 searches. Data last updated 17 September 2025.
Use the filters below to find and compare flights from Regina to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 20/10

9:45 a.m.-10:39 p.m.

1 stop11h 54m

Chicago O'Hare Intl

Fri 24/10

2:53 p.m.-9:36 p.m.

1 stop7h 43m

C$ 296

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 20/10

10:15 a.m.-6:39 p.m.

1 stop7h 24m

Chicago O'Hare Intl

Fri 24/10

5:30 p.m.-5:01 p.m.

2 stops24h 31m

C$ 356

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 21/10

5:30 p.m.-4:43 p.m.

2 stops46h 13m

Chicago O'Hare Intl

Fri 24/10

5:30 p.m.-11:01 p.m.

1 stop6h 31m

C$ 363

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 21/10

5:30 p.m.-4:43 p.m.

2 stops46h 13m

Chicago O'Hare Intl

Fri 24/10

5:30 p.m.-5:01 p.m.

2 stops24h 31m

C$ 398

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 20/10

2:25 p.m.-8:00 a.m.

2 stops16h 35m

Chicago O'Hare Intl

Fri 24/10

8:40 a.m.-6:13 p.m.

2 stops10h 33m

C$ 923

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 23/10

8:35 a.m.-4:43 p.m.

1 stop7h 08m

C$ 151

ReginaChicago

YQR - ORD

YQRORD

Regina

Sun 26/10

5:10 a.m.-1:35 p.m.

1 stop7h 25m

C$ 154

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 21/10

11:25 a.m.-7:24 p.m.

1 stop6h 59m

C$ 171

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 30/10

9:45 a.m.-10:50 p.m.

1 stop12h 05m

C$ 175

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 20/10

9:45 a.m.-11:59 p.m.

1 stop13h 14m

C$ 182

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 15 resultsSorted by cheapest first
1
2

See travel insights to Chicago from

How to get the cheapest flight ticket from Regina to Chicago

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 month to fly to Chicago?

The month of October is another great option to travel to Chicago, with average flight prices from Regina averaging around C$ 393.

What is the cheapest day to depart on your flight to Chicago?

The cheapest day to depart on your flight to Chicago is on a Saturday when prices can be found for as low as C$ 403. This is often the case because there is less demand to fly during this day of the week. If your travel schedule is flexible, try to avoid departing on a Sunday because tickets tend to average around C$ 946. These prices are subject to change though, so be sure to set up a Price Alert for flights to Chicago.

What is the cheapest time of day to depart on your flight to Chicago?

In the afternoon is the cheapest time of day to fly from Regina to Chicago when you can find flight prices for as low as C$ 460. Flying to Chicago in the afternoon is an ideal time because this is during off-peak travel hours. In the morning is when there is more demand to fly to Chicago, so prices are often more expensive at around C$ 696 per ticket.

When to book flights from Regina to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Regina to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Regina to Chicago (YQR to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Regina to Chicago

Direct flights

None
There are no direct flights from Regina to Chicago. There are no popular flight routes from Regina to Chicago.
Search flight deals

  • How far is Regina to Chicago by plane?

    The distance between Regina and Chicago is about 1611.7 km. By plane, this route typically takes 7h 24m.

  • When did momondo last update prices for flights from Regina Airport to Chicago?

    Prices for flights from Regina Airport to Chicago were last updated today.

  • How many operators does momondo search for flights from Regina Airport to Chicago?

  • How old do you have to be to fly from Regina Airport to Chicago?

    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.

  • What documentation or ID do you need to fly to Chicago?

    The travel and health documents you'll need for your trip to Chicago 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. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular airline from Regina to Chicago?

Best airlines flying from Regina to Chicago

Compare and see reviews for airlines that fly from Regina to Chicago with momondo
Airline
Rating
Free Cancellation
Price
WestJetPriceFrom C$ 372Free CancellationRating
7.2
3,095 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 399Free CancellationRating
7.1
10,000 reviews
Search Air Canada flights
DeltaPriceFrom C$ 462Free CancellationRating
7.9
7,961 reviews
Search Delta flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Munster
Hammond
Merrillville

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?

Yes. momondo allows you to filter the results for Regina to Chicago flights to just show those with flexible booking policies.

How can momondo help me find flights from Regina to Chicago?

Once all potential Regina to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

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.

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 17/10
Fri 24/10
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 25.6 km from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport