Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Regina to Chicago from C$ 163

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 11/5. 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

Enter your travel dates to find the best prices.
WestJet Logo
5:10 a.m. - 1:35 p.m.
YQR
-
ORD
7h 25m
1 stop
WestJet Logo
2:20 p.m. - 8:06 p.m.
ORD
-
YQR
6h 46m
1 stop
C$ 243WestJet
Fri, 10 Apr - Fri, 17 Apr
WestJet Logo
7:00 a.m. - 4:40 p.m.
YQR
-
ORD
8h 40m
1 stop
WestJet Logo
5:30 p.m. - 1:10 a.m.
ORD
-
YQR
8h 40m
1 stop
C$ 290WestJet
Thu, 28 May - Sun, 31 May
WestJet Logo
11:50 a.m. - 4:40 p.m.
YQR
-
ORD
27h 50m
2 stops
WestJet Logo
5:30 p.m. - 1:10 a.m.
ORD
-
YQR
8h 40m
1 stop
C$ 316WestJet
Thu, 28 May - Sun, 31 May
WestJet Logo
8:20 p.m. - 4:40 p.m.
YQR
-
ORD
19h 20m
2 stops
WestJet Logo
5:30 p.m. - 11:15 a.m.
ORD
-
YQR
18h 45m
2 stops
C$ 398WestJet
Thu, 28 May - Sun, 31 May
United Airlines Logo
5:00 a.m. - 2:00 p.m.
YQR
-
ORD
8h 00m
1 stop
United Airlines Logo
2:05 p.m. - 9:30 p.m.
ORD
-
YQR
8h 25m
1 stop
C$ 425United Airlines
Mon, 30 Mar - Thu, 2 Apr
Delta Logo
11:35 a.m. - 6:40 p.m.
YQR
-
MDW
6h 05m
1 stop
Delta Logo
9:30 a.m. - 6:21 p.m.
MDW
-
YQR
9h 51m
1 stop
C$ 447Delta
Mon, 30 Mar - Thu, 2 Apr
Multiple Airlines Logo
5:10 a.m. - 6:08 a.m.
YQR
-
ORD
23h 58m
2 stops
Multiple Airlines Logo
6:40 p.m. - 6:31 p.m.
ORD
-
YQR
24h 51m
1 stop
C$ 521Multiple Airlines
Tue, 10 Mar - Fri, 13 Mar
Multiple Airlines Logo
6:00 a.m. - 2:30 p.m.
YQR
-
ORD
31h 30m
2 stops
Multiple Airlines Logo
6:25 p.m. - 6:21 p.m.
ORD
-
YQR
24h 56m
1 stop
C$ 527Multiple Airlines
Mon, 30 Mar - Thu, 2 Apr
Air Canada Logo
5:00 a.m. - 1:01 p.m.
YQR
-
ORD
7h 01m
1 stop
Air Canada Logo
8:40 p.m. - 9:39 a.m.
ORD
-
YQR
13h 59m
1 stop
C$ 607Air Canada
Tue, 10 Mar - Fri, 27 Mar
Delta Logo
11:35 a.m. - 6:40 p.m.
YQR
-
MDW
6h 05m
1 stop
Delta Logo
9:30 a.m. - 6:31 p.m.
MDW
-
YQR
10h 01m
1 stop
C$ 748Delta
Tue, 10 Mar - Fri, 13 Mar

United Airlines flights from Regina to Chicago

Our best United Airlines deals on Regina to Chicago flight tickets
United Airlines
30 Mar
YQR5:00 a.m.Regina
8h 00m
1 stop
ORD2:00 p.m.Chicago O'Hare Intl
2 Apr
ORD2:05 p.m.Chicago O'Hare Intl
8h 25m
1 stop
YQR9:30 p.m.Regina
C$ 425
United Airlines
3 Mar
YQR10:45 a.m.Regina
6h 20m
1 stop
ORD5:05 p.m.Chicago O'Hare Intl
4 Mar
ORD2:40 p.m.Chicago O'Hare Intl
8h 11m
1 stop
YQR10:51 p.m.Regina
C$ 517
United Airlines
10 Mar
YQR9:45 a.m.Regina
9h 15m
1 stop
ORD8:00 p.m.Chicago O'Hare Intl
27 Mar
ORD9:15 p.m.Chicago O'Hare Intl
25h 36m
2 stops
YQR9:51 p.m.Regina
C$ 745

WestJet flights from Regina to Chicago

Our best WestJet deals on Regina to Chicago flight tickets
WestJet
10 Apr
YQR5:10 a.m.Regina
7h 25m
1 stop
ORD1:35 p.m.Chicago O'Hare Intl
17 Apr
ORD2:20 p.m.Chicago O'Hare Intl
6h 46m
1 stop
YQR8:06 p.m.Regina
C$ 243
WestJet
28 May
YQR7:00 a.m.Regina
8h 40m
1 stop
ORD4:40 p.m.Chicago O'Hare Intl
31 May
ORD5:30 p.m.Chicago O'Hare Intl
8h 40m
1 stop
YQR1:10 a.m.Regina
C$ 290
WestJet
28 May
YQR11:50 a.m.Regina
27h 50m
2 stops
ORD4:40 p.m.Chicago O'Hare Intl
31 May
ORD5:30 p.m.Chicago O'Hare Intl
8h 40m
1 stop
YQR1:10 a.m.Regina
C$ 316

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 27 February 2026.
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

Fri 10/4

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

1 stop7h 25m

Chicago O'Hare Intl

Fri 17/4

2:20 p.m.-8:06 p.m.

1 stop6h 46m

C$ 243

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 28/5

7:00 a.m.-4:40 p.m.

1 stop8h 40m

Chicago O'Hare Intl

Sun 31/5

5:30 p.m.-1:10 a.m.

1 stop8h 40m

C$ 290

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 28/5

11:50 a.m.-4:40 p.m.

2 stops27h 50m

Chicago O'Hare Intl

Sun 31/5

5:30 p.m.-1:10 a.m.

1 stop8h 40m

C$ 316

ReginaChicago

YQR - ORD

YQRORD

Regina

Thu 28/5

8:20 p.m.-4:40 p.m.

2 stops19h 20m

Chicago O'Hare Intl

Sun 31/5

5:30 p.m.-11:15 a.m.

2 stops18h 45m

C$ 398

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 30/3

5:00 a.m.-2:00 p.m.

1 stop8h 00m

Chicago O'Hare Intl

Thu 2/4

2:05 p.m.-9:30 p.m.

1 stop8h 25m

C$ 425

ReginaChicago

YQR - MDW

YQRMDW

Regina

Mon 30/3

11:35 a.m.-6:40 p.m.

1 stop6h 05m

Chicago Midway

Thu 2/4

9:30 a.m.-6:21 p.m.

1 stop9h 51m

C$ 447

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 10/3

5:10 a.m.-6:08 a.m.

2 stops23h 58m

Chicago O'Hare Intl

Fri 13/3

6:40 p.m.-6:31 p.m.

1 stop24h 51m

C$ 521

ReginaChicago

YQR - ORD

YQRORD

Regina

Mon 30/3

6:00 a.m.-2:30 p.m.

2 stops31h 30m

Chicago O'Hare Intl

Thu 2/4

6:25 p.m.-6:21 p.m.

1 stop24h 56m

C$ 527

ReginaChicago

YQR - ORD

YQRORD

Regina

Tue 10/3

5:00 a.m.-1:01 p.m.

1 stop7h 01m

Chicago O'Hare Intl

Fri 27/3

8:40 p.m.-9:39 a.m.

1 stop13h 59m

C$ 607

ReginaChicago

YQR - MDW

YQRMDW

Regina

Tue 10/3

11:35 a.m.-6:40 p.m.

1 stop6h 05m

Chicago Midway

Fri 13/3

9:30 a.m.-6:31 p.m.

1 stop10h 01m

C$ 748

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$ 379.

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

Fastest flight time

6h 05m

Direct flights

None
The fastest flight from Regina to Chicago takes 6h 05m
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 6h 05m.

  • 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
United AirlinesPriceFrom C$ 308Free CancellationRating
7.4
9,349 reviews
Search United Airlines 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
Sun 29/3
Sun 5/4
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