There are 8 ways to get from Regina to Chicago by plane, bus, car, or train
Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.
Fly to Chicago O'Hare International Airport
best- Fly from Regina (YQR) to Chicago O'Hare International Airport (ORD)plane YQR - ORD
6h 47m$129–791Bus, drive, train
- Take the bus from Regina to Lethbridgebus
- Drive from Lethbridge to Port of Sweet Grasscar
- Take the bus from Port of Sweet Grass to Shelby Transit Centerbus
- Take the train from Shelby Amtrak Station to Chicago Union Stationtrain
40h 7m$241–436Drive 1,147.8 mi
- Drive from Regina to Chicagocar 1,147.8 mi
19h 59m$263–380Fly to Chicago Midway International Airport
- Fly from Regina (YQR) to Chicago Midway International Airport (MDW)plane YQR - MDW
6h 41m$134–645Fly to South Bend, train
- Fly from Regina (YQR) to South Bend (SBN)plane YQR - SBN
- Take the train from South Bend Airport to Van Buren St.train
11h 6m$169–762Fly to General Mitchell International Airport, train
- Fly from Regina (YQR) to General Mitchell International Airport (MKE)plane YQR - MKE
- Take the train from Milwaukee to Chicago Union Stationtrain
8h 52m$241–1,186Bus, train via Detroit
- Take the bus from Regina, SK - 2820B Avonhurst to Portage la Prairie, MBbus
- Take the train from Portage la Prairie to Toronto Union Stationtrain
- Take the bus from Toronto to Detroit Bus Stationbus
- Take the bus from Detroit Bus Station to Chicago Bus Stationbus
2d 17h$301–458Bus, train
- Take the bus from Regina, SK - 2820B Avonhurst to Portage la Prairie, MBbus
- Take the train from Portage la Prairie to Toronto Union Stationtrain
- Take the train from Toronto Union Station to Buffalotrain
- Take the train from Buffalo Depew Station to Chicago Union Stationtrain
2d 18h$314–578
Regina (YQR) to Chicago O'Hare International Airport (ORD) flights
Questions & Answers
The cheapest way to get from Regina to Chicago is to drive which costs $260 - $380 and takes 19h 59m.
The fastest way to get from Regina to Chicago is to fly which takes 6h 41m and costs $130 - $650.
The distance between Regina and Chicago is 1011 miles. The road distance is 1154.5 miles.
The best way to get from Regina to Chicago without a car is to bus and train via Detroit which takes 2 days 17h and costs $300 - $460.
It takes approximately 6h 47m to get from Regina to Chicago, including transfers.
Yes, the driving distance between Regina to Chicago is 1154 miles. It takes approximately 19h 59m to drive from Regina to Chicago.
There are 1304+ hotels available in Chicago.
What companies run services between Regina, SK, Canada and Chicago, IL, USA?
Air Canada, United Airlines, and two other airlines fly from Regina (YQR) to Chicago O'Hare International Airport (ORD) 4 times a day.
- Website
- westjet.com
Flights from Regina to Chicago O'Hare International Airport via Minneapolis
- Ave. Duration
- 6h 26m
- When
- Every day
- Estimated price
- $120–600
Flights from Regina to Chicago O'Hare International Airport via Calgary
- Ave. Duration
- 7h 25m
- When
- Monday and Friday
- Estimated price
- $120–600
Flights from Regina to Chicago Midway International Airport via Minneapolis
- Ave. Duration
- 7h 5m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $200–1,400
Flights from Regina to Chicago Midway International Airport via Winnipeg, Minneapolis
- Ave. Duration
- 11h 35m
- When
- Monday to Friday
- Estimated price
- $130–650
Flights from Regina to South Bend via Minneapolis
- Ave. Duration
- 10h 3m
- When
- Every day
- Estimated price
- $240–1,600
Flights from Regina to South Bend via Winnipeg, Minneapolis
- Ave. Duration
- 14h 33m
- When
- Monday to Friday
- Estimated price
- $150–750
Flights from Regina to South Bend via Denver, Minneapolis
- Ave. Duration
- 10h 53m
- When
- Every day
- Estimated price
- $220–950
Flights from Regina to General Mitchell International Airport via Minneapolis
- Ave. Duration
- 6h 38m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $340–2,300
Flights from Regina to General Mitchell International Airport via Toronto, Detroit
- Ave. Duration
- 9h 8m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $450–2,500
Flights from Regina to General Mitchell International Airport via Calgary, Minneapolis
- Ave. Duration
- 10h 38m
- When
- Friday and Sunday
- Estimated price
- $460–2,500
Flights from Regina to General Mitchell International Airport via Winnipeg, Minneapolis
- Ave. Duration
- 11h 8m
- When
- Monday to Friday
- Estimated price
- $210–1,100
- Website
- delta.com
Flights from Regina to Chicago O'Hare International Airport via Minneapolis
- Ave. Duration
- 6h 26m
- When
- Every day
- Estimated price
- $120–600
Flights from Regina to Chicago O'Hare International Airport via Calgary
- Ave. Duration
- 7h 25m
- When
- Monday and Friday
- Estimated price
- $120–600
Flights from Regina to Chicago Midway International Airport via Minneapolis
- Ave. Duration
- 7h 5m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $200–1,400
Flights from Regina to South Bend via Minneapolis
- Ave. Duration
- 10h 3m
- When
- Every day
- Estimated price
- $240–1,600
Flights from Regina to South Bend via Toronto, Detroit
- Ave. Duration
- 12h 50m
- When
- Every day
- Estimated price
- $290–1,700
Flights from Regina to South Bend via Denver, Minneapolis
- Ave. Duration
- 10h 53m
- When
- Every day
- Estimated price
- $220–950
Flights from Regina to General Mitchell International Airport via Minneapolis
- Ave. Duration
- 6h 38m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $340–2,300
Flights from Regina to General Mitchell International Airport via Toronto, Detroit
- Ave. Duration
- 9h 8m
- When
- Monday, Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $450–2,500
- Website
- united.com
Flights from Regina to Chicago O'Hare International Airport via Toronto
- Ave. Duration
- 6h 40m
- When
- Monday, Tuesday, Wednesday, Friday, and Sunday
- Estimated price
- $110–600
Flights from Regina to Chicago O'Hare International Airport via Denver
- Ave. Duration
- 6h 20m
- When
- Every day
- Estimated price
- $110–500
Flights from Regina to Chicago O'Hare International Airport via Calgary
- Ave. Duration
- 6h 25m
- When
- Monday, Wednesday, Thursday, and Friday
- Estimated price
- $120–550
Flights from Regina to South Bend via Denver, Chicago O'Hare International Airport
- Ave. Duration
- 8h 8m
- When
- Every day
- Estimated price
- $210–950
Flights from Regina to General Mitchell International Airport via Denver
- Ave. Duration
- 10h 21m
- When
- Every day
- Estimated price
- $300–1,400
- Website
- southwest.com
Flights from Regina to Chicago Midway International Airport via Denver
- Ave. Duration
- 6h
- When
- Tuesday, Wednesday, Thursday, Friday, and Sunday
- Estimated price
- $170–800
Flights from Regina to Chicago Midway International Airport via Phoenix
- Ave. Duration
- 7h 50m
- When
- Thursday and Sunday
- Estimated price
- $260–1,100
Flights from Regina to Chicago Midway International Airport via Las Vegas
- Ave. Duration
- 12h 50m
- When
- Thursday
- Estimated price
- $260–1,100
Flights from Regina to General Mitchell International Airport via Denver
- Ave. Duration
- 5h 50m
- When
- Monday, Tuesday, and Thursday
- Estimated price
- $300–1,400
Flights from Regina to General Mitchell International Airport via Las Vegas
- Ave. Duration
- 7h 25m
- When
- Thursday
- Estimated price
- $440–1,800
Flights from Regina to General Mitchell International Airport via Phoenix
- Ave. Duration
- 8h 35m
- When
- Thursday
- Estimated price
- $450–1,800
- Website
- aircanada.com
Flights from Regina to Chicago O'Hare International Airport via Toronto
- Ave. Duration
- 6h 40m
- When
- Monday, Tuesday, Wednesday, Friday, and Sunday
- Estimated price
- $110–600
Flights from Regina to Chicago O'Hare International Airport via Calgary
- Ave. Duration
- 6h 25m
- When
- Monday, Wednesday, Thursday, and Friday
- Estimated price
- $120–550
Rome2Rio's guide to Amtrak
Contact Details
- Phone
- +1 800-872-7245
- Website
- amtrak.com
Train from Shelby Amtrak Station to Chicago Union Station
- Ave. Duration
- 28h 17m
- Frequency
- 3 times a day
- Estimated price
- $180–320
- Website
- https://www.amtrak.com/home.html
Train from Milwaukee to Chicago Union Station
- Ave. Duration
- 1h 29m
- Frequency
- Every 4 hours
- Estimated price
- $22–40
- Website
- https://www.amtrak.com/home.html
Train from Buffalo Depew Station to Chicago Union Station
- Ave. Duration
- 10h 33m
- Frequency
- Twice daily
- Estimated price
- $55–170
- Website
- https://www.amtrak.com/home.html
- Phone
- +1 219-926-5744
- Website
- mysouthshoreline.com
Train from South Bend Airport to Van Buren St.
- Ave. Duration
- 2h 1m
- Frequency
- Every 2 hours
- Estimated price
- $13–15
- Schedules at
- mysouthshoreline.com
- Adults 14-64
- $13–15
- Phone
- +1 888 842-7245
- Website
- viarail.ca
Train from Portage la Prairie to Toronto Union Station
- Ave. Duration
- 42h 14m
- Frequency
- Twice a week
- Estimated price
- $150–210
- Website
- https://www.viarail.ca/en
- Economy Adult - same day booking
- $150–210
- Economy Adult - Advanced Booking
- $180–210
- Economy Escape Advanced Booking - Adult
- $160–190
Train from Toronto Union Station to Buffalo
- Ave. Duration
- 4h 6m
- Frequency
- Once daily
- Estimated price
- $23–90
- Website
- https://www.viarail.ca/en
- Economy Adult - same day booking
- $26–90
- Economy Adult - Advanced Booking
- $26–70
- Economy Escape Advanced Booking - Adult
- $23–40
- Phone
- +1 (855) 626-8585
- Website
- flixbus.com
Bus from Regina to Lethbridge
- Ave. Duration
- 7h 45m
- Frequency
- 5 times a week
- Estimated price
- $45–95
- Schedules at
- flixbus.com
- Adult
- $45–95
Bus from Toronto to Detroit Bus Station
- Ave. Duration
- 6h 55m
- Frequency
- 4 times a day
- Estimated price
- $35–65
- Schedules at
- flixbus.com
Bus from Detroit Bus Station to Chicago Bus Station
- Ave. Duration
- 7h 50m
- Frequency
- Twice daily
- Estimated price
- $35–75
- Schedules at
- flixbus.com
- Phone
- +1 406-470-0727
- tctransit@gmail.com
- Website
- northern.rural-transit.com
Bus from Port of Sweet Grass to Shelby Transit Center
- Ave. Duration
- 45 min
- Frequency
- Once daily
- Schedules at
- northern.rural-transit.com
- Phone
- 1-833-583-3636
- contact@riderexpress.ca
- Website
- riderexpress.ca
Bus from Regina, SK - 2820B Avonhurst to Portage la Prairie, MB
- Ave. Duration
- 6h 41m
- Frequency
- Once daily
- Estimated price
- $75–100
- Website
- https://riderexpress.ca/
- Standard
- $75–100
Rome2Rio's guide to Greyhound USA
Contact Details
- Phone
- +1 214-849-8100
- ifsr@greyhound.com
- Website
- greyhound.com
Bus from Detroit Bus Station to Chicago Bus Station
- Ave. Duration
- 6h 5m
- Frequency
- 3 times a day
- Estimated price
- $30–60
- Website
- https://www.greyhound.com/
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