Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Regina to Chicago from C$ 225

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 30/9. 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

WestJet Logo
5:30 p.m. - 12:39 p.m.YQR-ORD
18h 09m1 stop
WestJet Logo
5:30 p.m. - 11:01 p.m.ORD-YQR
6h 31m1 stop
C$ 316WestJet
Find Deal
sex, 26 set - ter, 30 set
WestJet Logo
8:35 p.m. - 4:43 p.m.YQR-ORD
19h 08m1 stop
WestJet Logo
5:30 p.m. - 11:01 p.m.ORD-YQR
6h 31m1 stop
C$ 347WestJet
Find Deal
qui, 25 set - ter, 30 set
WestJet Logo
6:00 p.m. - 12:39 p.m.YQR-ORD
17h 39m2 stops
WestJet Logo
5:30 p.m. - 11:01 p.m.ORD-YQR
6h 31m1 stop
C$ 352WestJet
Find Deal
sex, 26 set - ter, 30 set
WestJet Logo
3:55 p.m. - 4:43 p.m.YQR-ORD
23h 48m2 stops
WestJet Logo
5:30 p.m. - 11:01 p.m.ORD-YQR
6h 31m1 stop
C$ 403WestJet
Find Deal
qui, 25 set - ter, 30 set
United Airlines Logo
10:45 a.m. - 4:58 p.m.YQR-ORD
6h 13m1 stop
United Airlines Logo
2:40 p.m. - 10:51 p.m.ORD-YQR
8h 11m1 stop
C$ 408United Airlines
Find Deal
sex, 21 nov - seg, 24 nov
Delta Logo
11:45 a.m. - 8:36 p.m.YQR-ORD
8h 51m2 stops
Delta Logo
12:17 p.m. - 6:17 p.m.ORD-YQR
6h 00m1 stop
C$ 434Delta
Find Deal
sex, 21 nov - seg, 24 nov
WestJet Logo
8:35 p.m. - 12:39 p.m.YQR-ORD
15h 04m2 stops
WestJet Logo
5:30 p.m. - 4:54 p.m.ORD-YQR
24h 24m2 stops
C$ 444WestJet
Find Deal
sex, 26 set - ter, 30 set
WestJet Logo
12:15 p.m. - 4:43 p.m.YQR-ORD
27h 28m2 stops
WestJet Logo
5:30 p.m. - 4:54 p.m.ORD-YQR
24h 24m2 stops
C$ 461WestJet
Find Deal
qui, 25 set - ter, 30 set
WestJet Logo
10:15 a.m. - 5:35 p.m.YQR-MDW
6h 20m1 stop
WestJet Logo
9:20 a.m. - 4:41 p.m.MDW-YQR
8h 21m1 stop
C$ 1,069WestJet
Find Deal
qui, 25 set - ter, 30 set
WestJet Logo
10:15 a.m. - 5:35 p.m.YQR-MDW
6h 20m1 stop
WestJet Logo
9:20 a.m. - 4:41 p.m.MDW-YQR
8h 21m1 stop
C$ 1,295WestJet
Find Deal
sex, 26 set - ter, 30 set

WestJet flights from Regina to Chicago

Our best WestJet deals on Regina to Chicago flight tickets
WestJet
26 Sep
YQR5:30 p.m.Regina
18h 09m
1 stop
ORD12:39 p.m.Chicago O'Hare Intl
30 Sep
ORD5:30 p.m.Chicago O'Hare Intl
6h 31m
1 stop
YQR11:01 p.m.Regina
C$ 316
Find similar
WestJet
25 Sep
YQR8:35 p.m.Regina
19h 08m
1 stop
ORD4:43 p.m.Chicago O'Hare Intl
30 Sep
ORD5:30 p.m.Chicago O'Hare Intl
6h 31m
1 stop
YQR11:01 p.m.Regina
C$ 347
Find similar
WestJet
26 Sep
YQR6:00 p.m.Regina
17h 39m
2 stops
ORD12:39 p.m.Chicago O'Hare Intl
30 Sep
ORD5:30 p.m.Chicago O'Hare Intl
6h 31m
1 stop
YQR11:01 p.m.Regina
C$ 352
Find similar

Delta flights from Regina to Chicago

Our best Delta deals on Regina to Chicago flight tickets
Delta
21 Nov
YQR11:45 a.m.Regina
8h 51m
2 stops
ORD8:36 p.m.Chicago O'Hare Intl
24 Nov
ORD12:17 p.m.Chicago O'Hare Intl
6h 00m
1 stop
YQR6:17 p.m.Regina
C$ 434
Find similar
Delta
23 Aug
YQR10:15 a.m.Regina
10h 20m
1 stop
ORD9:35 p.m.Chicago O'Hare Intl
27 Aug
ORD6:10 a.m.Chicago O'Hare Intl
11h 20m
1 stop
YQR4:30 p.m.Regina
C$ 887
Find similar
Delta
23 Aug
YQR10:15 a.m.Regina
23h 05m
2 stops
ORD10:20 a.m.Chicago O'Hare Intl
27 Aug
ORD2:00 p.m.Chicago O'Hare Intl
27h 30m
2 stops
YQR4:30 p.m.Regina
C$ 933
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 18 agosto 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

sex 26/9

5:30 p.m.-12:39 p.m.

1 stop18h 09m

Chicago O'Hare Intl

ter 30/9

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

1 stop6h 31m

C$ 316

ReginaChicago

YQR - ORD

YQRORD

Regina

qui 25/9

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

1 stop19h 08m

Chicago O'Hare Intl

ter 30/9

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

1 stop6h 31m

C$ 347

ReginaChicago

YQR - ORD

YQRORD

Regina

sex 26/9

6:00 p.m.-12:39 p.m.

2 stops17h 39m

Chicago O'Hare Intl

ter 30/9

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

1 stop6h 31m

C$ 352

ReginaChicago

YQR - ORD

YQRORD

Regina

qui 25/9

3:55 p.m.-4:43 p.m.

2 stops23h 48m

Chicago O'Hare Intl

ter 30/9

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

1 stop6h 31m

C$ 403

ReginaChicago

YQR - ORD

YQRORD

Regina

sex 21/11

10:45 a.m.-4:58 p.m.

1 stop6h 13m

Chicago O'Hare Intl

seg 24/11

2:40 p.m.-10:51 p.m.

1 stop8h 11m

C$ 408

ReginaChicago

YQR - ORD

YQRORD

Regina

sex 21/11

11:45 a.m.-8:36 p.m.

2 stops8h 51m

Chicago O'Hare Intl

seg 24/11

12:17 p.m.-6:17 p.m.

1 stop6h 00m

C$ 434

ReginaChicago

YQR - ORD

YQRORD

Regina

sex 26/9

8:35 p.m.-12:39 p.m.

2 stops15h 04m

Chicago O'Hare Intl

ter 30/9

5:30 p.m.-4:54 p.m.

2 stops24h 24m

C$ 444

ReginaChicago

YQR - ORD

YQRORD

Regina

qui 25/9

12:15 p.m.-4:43 p.m.

2 stops27h 28m

Chicago O'Hare Intl

ter 30/9

5:30 p.m.-4:54 p.m.

2 stops24h 24m

C$ 461

ReginaChicago

YQR - MDW

YQRMDW

Regina

qui 25/9

10:15 a.m.-5:35 p.m.

1 stop6h 20m

Chicago Midway

ter 30/9

9:20 a.m.-4:41 p.m.

1 stop8h 21m

C$ 1,069

ReginaChicago

YQR - MDW

YQRMDW

Regina

sex 26/9

10:15 a.m.-5:35 p.m.

1 stop6h 20m

Chicago Midway

ter 30/9

9:20 a.m.-4:41 p.m.

1 stop8h 21m

C$ 1,295

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 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 April is another great option to travel to Chicago, with average flight prices from Regina averaging around C$ 468.

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$ 405. 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$ 950. 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$ 462. 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$ 699 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

Best price found

C$ 225

Fastest flight time

6h 13m

Direct flights

None

Airports in Chicago

2 airports
The best one-way flight to Chicago from Regina in the past 72 hours is C$ 225. The best round-trip flight deal from Regina to Chicago found on momondo in the last 72 hours is C$ 316.
The fastest flight from Regina to Chicago takes 6h 13m
There are no direct flights from Regina to Chicago. Popular non-direct routes for this connection are Regina Airport - Chicago Midway Airport and Regina Airport - Chicago O'Hare Intl Airport.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
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 6h 13m.

  • 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$ 374Free CancellationRating
7.2
3,018 reviews
Search WestJet flights
Air CanadaPriceFrom C$ 403Free CancellationRating
7.1
9,992 reviews
Search Air Canada flights
DeltaPriceFrom C$ 464Free CancellationRating
8.0
7,981 reviews
Search Delta flights

Travelling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Hammond
Munster
Benton Harbor
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
sáb 23/8
sáb 30/8
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