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Cheap Flights from Regina (YQR) to Chicago (CHIA)

Compare Regina to Chicago flight deals

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Flight deals from Regina to Chicago

Looking for a cheap last-minute deal or the best return flight from Regina Airport to Chicago? If you want to travel next month, return fares start from $592. Find the lowest prices on one-way and return tickets right here.
Chicago.$520 per passenger.Departing Thu, 5 Nov, returning Mon, 9 Nov.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Regina on Thu, 5 Nov, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departs from Chicago O'Hare International on Mon, 9 Nov, arriving in Regina.Price includes taxes and charges.From $520, select.
Chicago.$530 per passenger.Departing Fri, 4 Sep, returning Mon, 7 Sep.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Regina on Fri, 4 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departs from Chicago O'Hare International on Mon, 7 Sep, arriving in Regina.Price includes taxes and charges.From $530, select.
Chicago.$538 per passenger.Departing Wed, 27 May, returning Wed, 3 Jun.Return flight with United.Outbound indirect flight with United, departs from Regina on Wed, 27 May, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Wed, 3 Jun, arriving in Regina.Price includes taxes and charges.From $538, select.
Chicago.$550 per passenger.Departing Mon, 31 Aug, returning Mon, 7 Sep.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Regina on Mon, 31 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departs from Chicago O'Hare International on Mon, 7 Sep, arriving in Regina.Price includes taxes and charges.From $550, select.
Chicago.$559 per passenger.Departing Tue, 11 Aug, returning Tue, 18 Aug.Return flight with WestJet.Outbound indirect flight with WestJet, departs from Regina on Tue, 11 Aug, arriving in Chicago O'Hare International.Inbound indirect flight with WestJet, departs from Chicago O'Hare International on Tue, 18 Aug, arriving in Regina.Price includes taxes and charges.From $559, select.
Chicago.$588 per passenger.Departing Tue, 22 Sep, returning Tue, 13 Oct.Return flight with Delta.Outbound indirect flight with Delta, departs from Regina on Tue, 22 Sep, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago Midway on Tue, 13 Oct, arriving in Regina.Price includes taxes and charges.From $588, select.
Chicago.$592 per passenger.Departing Mon, 1 Jun, returning Wed, 3 Jun.Return flight with Delta.Outbound indirect flight with Delta, departs from Regina on Mon, 1 Jun, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago Midway on Wed, 3 Jun, arriving in Regina.Price includes taxes and charges.From $592, select.
Chicago.$643 per passenger.Departing Fri, 29 May, returning Sat, 30 May.Return flight with Delta.Outbound indirect flight with Delta, departs from Regina on Fri, 29 May, arriving in Chicago O'Hare International.Inbound indirect flight with Delta, departs from Chicago Midway on Sat, 30 May, arriving in Regina.Price includes taxes and charges.From $643, select.
Chicago.$656 per passenger.Departing Wed, 29 Jul, returning Tue, 4 Aug.Return flight with United.Outbound indirect flight with United, departs from Regina on Wed, 29 Jul, arriving in Chicago O'Hare International.Inbound indirect flight with United, departs from Chicago O'Hare International on Tue, 4 Aug, arriving in Regina.Price includes taxes and charges.From $656, select.
Chicago.$661 per passenger.Departing Sun, 5 Jul, returning Mon, 13 Jul.Return flight with Delta.Outbound indirect flight with Delta, departs from Regina on Sun, 5 Jul, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Mon, 13 Jul, arriving in Regina.Price includes taxes and charges.From $661, select.
Chicago.$744 per passenger.Departing Thu, 8 Oct, returning Sun, 11 Oct.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Regina on Thu, 8 Oct, arriving in Chicago O'Hare International.Inbound indirect flight with Air Canada, departs from Chicago O'Hare International on Sun, 11 Oct, arriving in Regina.Price includes taxes and charges.From $744, select.
Chicago.$925 per passenger.Departing Fri, 15 Jan, returning Mon, 15 Feb.Return flight with Air Canada.Outbound indirect flight with Air Canada, departs from Regina on Fri, 15 Jan, arriving in Chicago O'Hare International.Inbound indirect flight with Air Canada, departs from Chicago O'Hare International on Mon, 15 Feb, arriving in Regina.Price includes taxes and charges.From $925, select.
Chicago.$1,010 per passenger.Departing Fri, 26 Jun, returning Sun, 5 Jul.Return flight with Delta.Outbound indirect flight with Delta, departs from Regina on Fri, 26 Jun, arriving in Chicago Midway.Inbound indirect flight with Delta, departs from Chicago Midway on Sun, 5 Jul, arriving in Regina.Price includes taxes and charges.From $1,010, select.

Find the cheapest month to fly from Regina to Chicago

We’re always keeping an eye on fares, so you can find the best one in seconds. It looks like Regina to Chicago flights are currently cheapest in November.
May
from $643
Jun
from $592
Jul
from $661
Aug
from $559
Sep
from $530
Oct
from $744
Nov
from $520
Dec
Find prices
Jan
Find prices
Feb
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Mar
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Apr
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Alternative Regina to Chicago routes

Looking for the cheapest, fastest or easiest route from Regina to Chicago? You could fly into the following airports instead.

Chicago Midway

14km from central Chicago
Closest
from $596
Search flights

Chicago O'Hare International

25km from central Chicago
Cheapest
from $520
Search flights

Chicago Dupage County

51km from central Chicago
Search flights

Chicago Rockford

126km from central Chicago
Search flights

Regina to Chicago: Flight information

The things to know before you go.
Cheapest flight found$520
Cheapest month to flyNovember

Finding cheap flights from Regina to Chicago: Frequently asked questions

There are 4 airports in Chicago: Chicago Midway, Chicago O'Hare International, Chicago Dupage County, and Chicago Rockford.
The best price we found for a return flight from Regina to Chicago is $520. This is an estimate based on information collected from different airlines and travel providers over the last 4 days and is subject to change and availability.
Currently, there are no airlines that fly direct from Regina to Chicago. But we found flights with one or more stops from $520.
As of May 2026, there are no flights flying from Regina to Chicago.
The cheapest month to fly from Regina to Chicago is usually November.
If you're flying from Regina Airport, the cheapest airport near Chicago is Chicago O'Hare International – which is 25.4 km away from the centre of Chicago. We've found flights into this airport from $520.
After crunching the numbers on our flight calendar, we found that it's currently cheapest to fly from Regina Airport to Chicago on Thursday, 5 November 2026.
No airlines currently offer direct flights between Regina Airport and Chicago. Most routes have one or more stops.
We show every price from over 1,200 airlines and travel agents, comparing them all so you don’t have to. If you know you want to fly to Chicago but you’re not ready to book, set up a Price Alert. We’ll track prices for you, and let you know when they rise or fall.
We crunched all the numbers in our flight calendar and it looks like the cheapest time to book a flight to Chicago is around 40 days in advance, so don’t leave your flight to the last minute.
In May, the average temperature is usually around 13°C. July is typically the warmest month in Chicago, when it usually averages around 26°C. You can expect the least rain in January. The coldest month is January, with temperatures averaging -8°C. The rainiest month is August.
Currently, WestJet offers the cheapest flight tickets to Chicago.

Travelling from Regina International Airport (YQR) to Chicago: what you need to know

  • The timezone in Chicago is UTC-5. The city is one hour ahead of Regina, where Regina International Airport is located.

  • For stress-free travel, turn up at the airport two hours ahead of international flights and an hour before domestic departures. That way, you won't have to rush to board your YQR to Chicago flight.

  • Travelling during a peak time like August? Public holidays and other popular seasons can lead to longer lines at check-in and security. Be extra cautious and get there up to four hours ahead of an international flight and two hours before a domestic departure.

  • Located around 3 kilometres from the centre of Regina, YQR can be reached in about 10 minutes by car, depending on traffic. Travelling on public transport will take roughly 35 minutes.

  • In search of a hotel near YQR? If you've booked an early flight from Regina International Airport to Chicago, these accommodation options will get you from your pillow to the plane in no time:

  • Of the departures from Regina International Airport, 58.83% land on schedule at their destination.

How to find the cheapest flights from Regina International Airport (YQR) to Chicago

  • $270 is the cheapest price we've found for a one-way Regina International Airport to Chicago flight. A return plane ticket right now is $520. Depending on when and how early you book, these fares can change.

  • To find cheap flights from YQR to Chicago, book as early as you can. Airlines usually offer the most competitive fares when flights first go on sale.

  • If you're willing to be flexible with your trip dates, take advantage of the 'Whole month' search tool. It'll give you the cheapest price across each month when looking for your Regina International Airport to Chicago ticket.

  • Finding a cheap flight from YQR to Chicago is easy with Price Alerts. Simply create one of these automatic notifications and we'll get in touch as soon as a new discount appears.

  • Tailor your trip with filters. Pick your ideal departure and arrival times, total journey duration and airlines. You can also sort your results by 'Best,' 'Fastest' or 'Cheapest' flights from Regina International Airport to Chicago.

Airports in Chicago

O'Hare International Airport (ORD)

  • O'Hare International Airport (ORD) is around 40 kilometres from central Chicago. If you're opting for a ride-share or a cab, the drive takes roughly 35 minutes.

  • It takes around 55 minutes if you're travelling by public transport.

  • If you have a late flight from Regina International Airport to Chicago, nothing beats the convenience of staying near the terminal. Pick up your bags from the carousel and then be showered and resting not long after at one of these accommodation options near ORD:

  • Grab an O'Hare International Airport rental car and explore Chicago and beyond with your own wheels. Routes Car Rentals, Dollar and Budget are leading providers you can book with here.

  • Lock in the best possible rate by reserving your vehicle from O'Hare International Airport about four weeks ahead of your flight from YQR to Chicago.

  • You'll find ORD at 10000 West O'Hare.

Chicago Midway International Airport (MDW)

  • Once your flight from Regina International Airport to Chicago has landed, you can make your way to the city centre in about 20 minutes by car. Central Chicago is roughly 19 kilometres from Chicago Midway International Airport (MDW).

  • The trip will take roughly 45 minutes on public transport.

  • After stepping off your YQR to Chicago flight, unwind at a hotel near MDW. These are some great accommodation options that'll help you switch to relaxation mode:

  • Forget about inconvenient public transport timetables or waiting in a long cab line. Pick up a Chicago Midway International Airport rental car and let your trip unfold on your terms. Check out the availability and rates from Dollar, Hertz and Budget.

  • Don't pay more than you need to. Booking your ride four weeks before your arrival at MDW will save you money.

  • Chicago Midway International Airport can be found at 5700 South Cicero.

Chicago Rockford International Airport (RFD)

  • Step off your flight from Regina International Airport to Chicago and make your way to your hotel or start sightseeing right away. Central Chicago is around 137 kilometres from Chicago Rockford International Airport (RFD) and typically takes 1 hour 25 minutes to reach driving.

  • The journey will take about 4 hours 15 minutes when travelling on public transport.

  • Enjoy a quiet, low-key start to your break by choosing a hotel near RFD after your YQR to Chicago flight. Rest up after a long day of travel or simply take a moment to get your footing in a new city at:

  • Whether you'd like a compact for a solo getaway or an SUV to fit the family, you'll find the right Chicago Rockford International Airport rental car for you. Browse the types of wheels available here from companies such as Budget, Alamo and National.

  • Rental companies sometimes offer deals for early bookings, so reserve your vehicle from RFD ahead of your flight from Regina International Airport to Chicago. A little prep work can make a big difference in cost.

  • The street address for Chicago Rockford International Airport is 2 Airport Cir.

Best time to go to Chicago

  • Plan your trip to Chicago during high season if you prefer a bustling atmosphere, but remember that hotel prices may be higher. Alternatively, book your flights from Regina International Airport to Chicago during the off-season when prices are cheaper and it's not as busy.

  • Book a Regina International Airport to Chicago flight ticket with a departure in July if you want to explore the city during its warmest month. You can expect temperatures to range from 15ºC (59ºF) to 29ºC (84ºF).

  • January has average temperatures of between -12ºC (10ºF) and 3ºC (37ºF). Look for a cheap ticket from YQR to Chicago around that time if you'd rather travel in cooler conditions.

More about Chicago

  • After booking your flight from Regina International Airport to Chicago, find a hotel that offers the right mix of comfort and location. Make one of these accommodation options your base for exploring Chicago:

  • There are so many things to discover in this city it can be tricky to work out where to begin. Art Institute of Chicago, Millennium Park and LandShark Beer Garden at Navy Pier are major attractions which should feature on any good Chicago itinerary.

Explore more of United States

  • Columbus is just one of the many places in United States waiting to be explored after you've experienced Chicago. Around 451 kilometres away to the south-east, popular attractions include Franklin Park Conservatory and Botanical Gardens, Ohio Statehouse and German Village.

  • If you want to check out another great destination in United States, consider Indianapolis, roughly 257 kilometres south-east of Chicago. The Children's Museum of Indianapolis, Indianapolis Museum of Art and Indianapolis Zoo are key reasons to visit.

Plan the rest of your trip from Regina to Chicago

Prices shown on this page are estimated lowest prices only. Found in the last 45 days.