There are 5 ways to get from Calgary to Chicago by plane, bus, train or car

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2rio's travel planner.

Recommended option

Fly to Chicago O'Hare  •  6 h 46 min

  1. Fly from Calgary (YYC) to Chicago O'Hare (ORD) YYC - ORD

$210 - $453

4 alternative options

Fly to Chicago Midway  •  8 h 49 min

  1. Fly from Calgary (YYC) to Chicago Midway (MDW) YYC - MDW

$240 - $482

Bus, Amtrak Thruway  •  2 days 10 h

  1. Take the bus from Calgary, AB to Sault Ste Marie, ON
  2. Take the Amtrak Thruway from Sault Ste. Marie, MI to Kalamazoo, MI - Amtrak
  3. Take the bus from Kalamazoo to Chicago Union Station

Bus, train  •  2 days 14 h

  1. Take the bus from Calgary, AB to Coquitlam, BC
  2. Take the bus from Coquitlam, Bc to Everett, Wa
  3. Take the train from Everett Amtrak to Chicago Union Station Amtrak

$331 - $970

Drive  •  27 h 43 min

  1. Drive from Calgary to Chicago 1703.7 miles

$220 - $330

What companies run services between Calgary, AB, Canada and Chicago, IL, USA?

WestJet, American Airlines and four other airlines fly from Calgary to Chicago hourly. Alternatively, you can take a bus from Calgary to Chicago via Sault Ste Marie, ON, Sault Ste. Marie, MI, Kalamazoo, MI - Amtrak, and Kalamazoo in around 2 days 10 h.

Airlines
Air Canada
Website
aircanada.com
Flights from Calgary to Chicago O'Hare
Ave. Duration
3 h 35 min
When
Every day
Estimated price
$270 - $950
Flights from Calgary to Chicago O'Hare via Denver
Ave. Duration
6 h 13 min
When
Every day
Estimated price
$270 - $950
Flights from Calgary to Chicago O'Hare via Toronto
Ave. Duration
6 h 49 min
When
Every day
Estimated price
$280 - $1,000
Flights from Calgary to Chicago O'Hare via Vancouver
Ave. Duration
6 h 59 min
When
Every day
Estimated price
$280 - $1,000
Delta
Website
delta.com
Flights from Calgary to Chicago O'Hare
Ave. Duration
3 h 26 min
When
Monday, Wednesday, Thursday, Friday, Saturday and Sunday
Estimated price
$380 - $950
Flights from Calgary to Chicago O'Hare via Minneapolis
Ave. Duration
5 h 34 min
When
Every day
Estimated price
$290 - $800
Flights from Calgary to Chicago O'Hare via Salt Lake City
Ave. Duration
6 h 4 min
When
Sunday
Estimated price
$290 - $800
Flights from Calgary to Chicago Midway via Minneapolis
Ave. Duration
5 h 44 min
When
Every day
Estimated price
$290 - $750
Flights from Calgary to Chicago Midway via Minneapolis, Detroit
Ave. Duration
9 h 3 min
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$290 - $750
United Airlines
Website
united.com
Flights from Calgary to Chicago O'Hare
Ave. Duration
3 h 35 min
When
Every day
Estimated price
$270 - $950
Flights from Calgary to Chicago O'Hare via Denver
Ave. Duration
6 h 13 min
When
Every day
Estimated price
$270 - $950
Southwest Airlines
Website
southwest.com
Flights from Calgary to Chicago Midway via Denver
Ave. Duration
6 h 27 min
When
Sunday
Estimated price
$160 - $800
Flights from Calgary to Chicago Midway via Seattle
Ave. Duration
6 h 55 min
When
Sunday
Estimated price
$190 - $700
American Airlines
Website
aa.com
Flights from Calgary to Chicago O'Hare
Ave. Duration
3 h 35 min
When
Monday, Wednesday, Thursday, Friday, Saturday and Sunday
Estimated price
$240 - $700
Flights from Calgary to Chicago O'Hare via Dallas/Ft.Worth
Ave. Duration
7 h 20 min
When
Every day
Estimated price
$240 - $700
WestJet
Website
westjet.com
Flights from Calgary to Chicago O'Hare
Ave. Duration
3 h 26 min
When
Monday, Wednesday, Thursday, Friday, Saturday and Sunday
Estimated price
$380 - $950
Alaska Airlines, Inc.
Website
alaskaair.com
Flights from Calgary to Chicago O'Hare via Seattle
Ave. Duration
7 h 23 min
When
Every day
Estimated price
$320 - $800
Train operators
Amtrak
Phone
+1 1-800-872-7245
Website
amtrak.com
Train from Everett Amtrak to Chicago Union Station Amtrak
Ave. Duration
44 h 16 min
Frequency
Once daily
Estimated price
$260 - $800
Website
amtrak.com
Coach Seat
$260 - $390
Flexi Coach Seat
$470 - $700
Business Coach Seat
$550 - $800
Room
$1,000 - $1,400
Bus operators
Greyhound Canada
Phone
+1 1-800-661-8747
Email
Canada.info@greyhound.ca
Website
greyhound.ca
Bus from Calgary, AB to Sault Ste Marie, ON
Ave. Duration
43 h 20 min
Frequency
Once daily
Estimated price
$140 - $350
Website
Greyhound.ca
Advanced Purchase
$140 - $210
Online Fare
$190 - $270
Standard Fare
$240 - $350
Refundable
$260 - $370
Bus from Calgary, AB to Coquitlam, BC
Ave. Duration
13 h 45 min
Frequency
Twice daily
Estimated price
$50 - $130
Website
Greyhound.ca
Advanced Purchase
$50 - $80
Online Fare
$70 - $110
Standard Fare
$90 - $130
Refundable
$100 - $150
Indian Trails
Phone
+1 800-292-3831
Website
indiantrails.com
Bus from Kalamazoo to Chicago Union Station
Ave. Duration
3 h 15 min
Frequency
Twice daily
Estimated price
$22 - $30
Schedules at
indiantrails.com
Book at
webstore.indiantrails.com
Greyhound USA
Phone
+1 214-849-8100
Email
ifsr@greyhound.com
Website
greyhound.com
Bus from Coquitlam, Bc to Everett, Wa
Ave. Duration
3 h 10 min
Frequency
Hourly
Estimated price
$16 - $40
Website
greyhound.com
Economy
$16 - $25
Flexible
$29 - $40

Want to know more about travelling around United States

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Questions & Answers

The distance between Calgary and Chicago is 2252 km. The road distance is 2726 km.

The cheapest way to get from Calgary to Chicago is to drive which costs $290 - $420 and takes 27 h 43 min.

The quickest way to get from Calgary to Chicago is to fly which takes 6 h 46 min and costs $270 - $600.

It takes approximately 6 h 46 min to get from Calgary to Chicago, including transfers.