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Cheap Flights from Calgary to Chicago from C$369

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Find cheap flights from Calgary (YYC) to Chicago (ORD)

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Thu, 25 Apr - Mon, 29 Apr

Calgary (YYC)

to

Chicago (ORD)

C$369

roundtrip

found 4 hours ago

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Sat, 6 Apr - Mon, 8 Apr

Calgary (YYC)

to

Chicago (ORD)

C$374

roundtrip

found 1 day ago

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Wed, 27 Feb - Wed, 6 Mar

Calgary (YYC)

to

Chicago (ORD)

C$376

roundtrip

found 8 hours ago

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Fri, 1 Mar - Sun, 3 Mar

Calgary (YYC)

to

Chicago (ORD)

C$378

roundtrip

found 3 hours ago

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Fri, 5 Apr - Wed, 10 Apr

Calgary (YYC)

to

Chicago (ORD)

C$381

roundtrip

found 6 hours ago

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Thu, 25 Apr - Mon, 29 Apr

Calgary (YYC)

to

Chicago (ORD)

C$386

roundtrip

found 4 hours ago

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Fri, 1 Mar - Sun, 3 Mar

Calgary (YYC)

to

Chicago (ORD)

C$388

roundtrip

found 3 hours ago

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Tue, 12 Feb - Tue, 19 Feb

Calgary (YYC)

to

Chicago (ORD)

C$401

roundtrip

found 4 days ago

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Wed, 13 Feb - Wed, 20 Feb

Calgary (YYC)

to

Chicago (ORD)

C$402

roundtrip

found 3 days ago

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Wed, 17 Apr - Sun, 21 Apr

Calgary (YYC)

to

Chicago (ORD)

C$405

roundtrip

found 1 day ago

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Tue, 19 Feb - Fri, 22 Feb

Calgary (YYC)

to

Chicago (ORD)

C$406

roundtrip

found 21 hours ago

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Tue, 16 Apr - Thu, 25 Apr

Calgary (YYC)

to

Chicago (ORD)

C$407

roundtrip

found 21 hours ago

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Fri, 5 Apr - Wed, 10 Apr

Calgary (YYC)

to

Chicago (ORD)

C$408

roundtrip

found 6 hours ago

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Thu, 7 Mar - Wed, 20 Mar

Calgary (YYC)

to

Chicago (ORD)

C$410

roundtrip

just found

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Tue, 16 Apr - Thu, 25 Apr

Calgary (YYC)

to

Chicago (ORD)

C$411

roundtrip

found 21 hours ago

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Thu, 14 Mar - Tue, 19 Mar

Calgary (YYC)

to

Chicago (ORD)

C$412

roundtrip

found 5 days ago

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Fri, 8 Feb - Mon, 11 Feb

Calgary (YYC)

to

Chicago (ORD)

C$413

roundtrip

found 3 days ago

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Mon, 1 Apr - Sun, 7 Apr

Calgary (YYC)

to

Chicago (ORD)

C$414

roundtrip

found 5 days ago

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Fri, 8 Feb - Mon, 11 Feb

Calgary (YYC)

to

Chicago (ORD)

C$415

roundtrip

found 3 days ago

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Tue, 16 Apr - Thu, 25 Apr

Calgary (YYC)

to

Chicago (ORD)

C$417

roundtrip

found 21 hours ago

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Thu, 7 Mar - Wed, 13 Mar

Calgary (YYC)

to

Chicago (ORD)

C$419

roundtrip

found 16 hours ago

Open YYC to ORD flights search result page
Thu, 7 Mar - Wed, 13 Mar

Calgary (YYC)

to

Chicago (ORD)

C$421

roundtrip

found 16 hours ago

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Thu, 28 Feb - Mon, 4 Mar

Calgary (YYC)

to

Chicago (ORD)

C$422

roundtrip

found 3 days ago

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Wed, 13 Feb - Wed, 20 Feb

Calgary (YYC)

to

Chicago (ORD)

C$427

roundtrip

found 3 days ago

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Tue, 16 Apr - Thu, 25 Apr

Calgary (YYC)

to

Chicago (ORD)

C$428

roundtrip

found 21 hours ago

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Thu, 21 Feb - Wed, 27 Feb

Calgary (YYC)

to

Chicago (ORD)

C$431

roundtrip

found 2 days ago

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Tue, 5 Mar - Sun, 10 Mar

Calgary (YYC)

to

Chicago (ORD)

C$433

roundtrip

found 1 day ago

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Thu, 7 Mar - Wed, 20 Mar

Calgary (YYC)

to

Chicago (ORD)

C$434

roundtrip

just found

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Tue, 16 Apr - Thu, 25 Apr

Calgary (YYC)

to

Chicago (ORD)

C$435

roundtrip

found 21 hours ago

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Fri, 24 May - Mon, 27 May

Calgary (YYC)

to

Chicago (ORD)

C$436

roundtrip

found 2 days ago

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Thu, 7 Mar - Wed, 13 Mar

Calgary (YYC)

to

Chicago (ORD)

C$437

roundtrip

found 16 hours ago

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Tue, 16 Apr - Thu, 25 Apr

Calgary (YYC)

to

Chicago (ORD)

C$440

roundtrip

found 21 hours ago

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Thu, 7 Mar - Wed, 13 Mar

Calgary (YYC)

to

Chicago (ORD)

C$441

roundtrip

found 16 hours ago

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Thu, 25 Apr - Mon, 29 Apr

Calgary (YYC)

to

Chicago (ORD)

C$443

roundtrip

found 4 hours ago

Open YYC to ORD flights search result page
Wed, 10 Apr - Tue, 16 Apr

Calgary (YYC)

to

Chicago (ORD)

C$443

roundtrip

found 1 day ago

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Mon, 25 Mar - Sat, 30 Mar

Calgary (YYC)

to

Chicago (ORD)

C$454

roundtrip

found 2 hours ago

Open YYC to ORD flights search result page
Mon, 4 Feb - Thu, 14 Feb

Calgary (YYC)

to

Chicago (ORD)

C$455

roundtrip

found 3 hours ago

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Thu, 24 Jan - Sun, 24 Feb

Calgary (YYC)

to

Chicago (ORD)

C$508

roundtrip

found 1 day ago

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Wed, 28 Aug - Tue, 10 Sep

Calgary (YYC)

to

Chicago (ORD)

C$545

roundtrip

found 6 days ago

Open YYC to ORD flights search result page
Mon, 28 Jan - Tue, 5 Feb

Calgary (YYC)

to

Chicago (ORD)

C$598

roundtrip

found 5 days ago

Open YYC to ORD flights search result page
Thu, 24 Jan - Sun, 24 Feb

Calgary (YYC)

to

Chicago (ORD)

C$508

roundtrip

found 1 day ago

Open YYC to ORD flights search result page
Mon, 28 Jan - Tue, 5 Feb

Calgary (YYC)

to

Chicago (ORD)

C$598

roundtrip

found 5 days ago

Open YYC to ORD flights search result page
Wed, 27 Feb - Wed, 6 Mar

Calgary (YYC)

to

Chicago (ORD)

C$376

roundtrip

found 8 hours ago

Open YYC to ORD flights search result page
Tue, 12 Feb - Tue, 19 Feb

Calgary (YYC)

to

Chicago (ORD)

C$401

roundtrip

found 4 days ago

Open YYC to ORD flights search result page
Wed, 13 Feb - Wed, 20 Feb

Calgary (YYC)

to

Chicago (ORD)

C$402

roundtrip

found 3 days ago

Open YYC to ORD flights search result page
Tue, 19 Feb - Fri, 22 Feb

Calgary (YYC)

to

Chicago (ORD)

C$406

roundtrip

found 21 hours ago

Open YYC to ORD flights search result page
Fri, 8 Feb - Mon, 11 Feb

Calgary (YYC)

to

Chicago (ORD)

C$413

roundtrip

found 3 days ago

Open YYC to ORD flights search result page
Fri, 8 Feb - Mon, 11 Feb

Calgary (YYC)

to

Chicago (ORD)

C$415

roundtrip

found 3 days ago

Open YYC to ORD flights search result page
Thu, 28 Feb - Mon, 4 Mar

Calgary (YYC)

to

Chicago (ORD)

C$422

roundtrip

found 3 days ago

Open YYC to ORD flights search result page
Wed, 13 Feb - Wed, 20 Feb

Calgary (YYC)

to

Chicago (ORD)

C$427

roundtrip

found 3 days ago

Open YYC to ORD flights search result page
Thu, 21 Feb - Wed, 27 Feb

Calgary (YYC)

to

Chicago (ORD)

C$431

roundtrip

found 2 days ago

Open YYC to ORD flights search result page
Mon, 4 Feb - Thu, 14 Feb

Calgary (YYC)

to

Chicago (ORD)

C$455

roundtrip

found 3 hours ago

Open YYC to ORD flights search result page
Fri, 1 Mar - Sun, 3 Mar

Calgary (YYC)

to

Chicago (ORD)

C$378

roundtrip

found 3 hours ago

Open YYC to ORD flights search result page
Fri, 1 Mar - Sun, 3 Mar

Calgary (YYC)

to

Chicago (ORD)

C$388

roundtrip

found 3 hours ago

Open YYC to ORD flights search result page
Thu, 7 Mar - Wed, 20 Mar

Calgary (YYC)

to

Chicago (ORD)

C$410

roundtrip

just found

Open YYC to ORD flights search result page
Thu, 14 Mar - Tue, 19 Mar

Calgary (YYC)

to

Chicago (ORD)

C$412

roundtrip

found 5 days ago

Open YYC to ORD flights search result page
Thu, 7 Mar - Wed, 13 Mar

Calgary (YYC)

to

Chicago (ORD)

C$419

roundtrip

found 16 hours ago

Open YYC to ORD flights search result page
Thu, 7 Mar - Wed, 13 Mar

Calgary (YYC)

to

Chicago (ORD)

C$421

roundtrip

found 16 hours ago

Open YYC to ORD flights search result page
Tue, 5 Mar - Sun, 10 Mar

Calgary (YYC)

to

Chicago (ORD)

C$433

roundtrip

found 1 day ago

Open YYC to ORD flights search result page
Thu, 7 Mar - Wed, 20 Mar

Calgary (YYC)

to

Chicago (ORD)

C$434

roundtrip

just found

Open YYC to ORD flights search result page
Thu, 7 Mar - Wed, 13 Mar

Calgary (YYC)

to

Chicago (ORD)

C$437

roundtrip

found 16 hours ago

Open YYC to ORD flights search result page
Thu, 7 Mar - Wed, 13 Mar

Calgary (YYC)

to

Chicago (ORD)

C$441

roundtrip

found 16 hours ago

Open YYC to ORD flights search result page
Mon, 25 Mar - Sat, 30 Mar

Calgary (YYC)

to

Chicago (ORD)

C$454

roundtrip

found 2 hours ago

Open YYC to ORD flights search result page
Thu, 25 Apr - Mon, 29 Apr

Calgary (YYC)

to

Chicago (ORD)

C$369

roundtrip

found 4 hours ago

Open YYC to ORD flights search result page
Sat, 6 Apr - Mon, 8 Apr

Calgary (YYC)

to

Chicago (ORD)

C$374

roundtrip

found 1 day ago

Open YYC to ORD flights search result page
Fri, 5 Apr - Wed, 10 Apr

Calgary (YYC)

to

Chicago (ORD)

C$381

roundtrip

found 6 hours ago

Open YYC to ORD flights search result page
Thu, 25 Apr - Mon, 29 Apr

Calgary (YYC)

to

Chicago (ORD)

C$386

roundtrip

found 4 hours ago

Open YYC to ORD flights search result page
Wed, 17 Apr - Sun, 21 Apr

Calgary (YYC)

to

Chicago (ORD)

C$405

roundtrip

found 1 day ago

Open YYC to ORD flights search result page
Tue, 16 Apr - Thu, 25 Apr

Calgary (YYC)

to

Chicago (ORD)

C$407

roundtrip

found 21 hours ago

Open YYC to ORD flights search result page
Fri, 5 Apr - Wed, 10 Apr

Calgary (YYC)

to

Chicago (ORD)

C$408

roundtrip

found 6 hours ago

Open YYC to ORD flights search result page
Tue, 16 Apr - Thu, 25 Apr

Calgary (YYC)

to

Chicago (ORD)

C$411

roundtrip

found 21 hours ago

Open YYC to ORD flights search result page
Mon, 1 Apr - Sun, 7 Apr

Calgary (YYC)

to

Chicago (ORD)

C$414

roundtrip

found 5 days ago

Open YYC to ORD flights search result page
Tue, 16 Apr - Thu, 25 Apr

Calgary (YYC)

to

Chicago (ORD)

C$417

roundtrip

found 21 hours ago

Open YYC to ORD flights search result page
Tue, 16 Apr - Thu, 25 Apr

Calgary (YYC)

to

Chicago (ORD)

C$428

roundtrip

found 21 hours ago

Open YYC to ORD flights search result page
Tue, 16 Apr - Thu, 25 Apr

Calgary (YYC)

to

Chicago (ORD)

C$435

roundtrip

found 21 hours ago

Open YYC to ORD flights search result page
Tue, 16 Apr - Thu, 25 Apr

Calgary (YYC)

to

Chicago (ORD)

C$440

roundtrip

found 21 hours ago

Open YYC to ORD flights search result page
Thu, 25 Apr - Mon, 29 Apr

Calgary (YYC)

to

Chicago (ORD)

C$443

roundtrip

found 4 hours ago

Open YYC to ORD flights search result page
Wed, 10 Apr - Tue, 16 Apr

Calgary (YYC)

to

Chicago (ORD)

C$443

roundtrip

found 1 day ago

Open YYC to ORD flights search result page
Fri, 24 May - Mon, 27 May

Calgary (YYC)

to

Chicago (ORD)

C$436

roundtrip

found 2 days ago

Open YYC to ORD flights search result page
Wed, 28 Aug - Tue, 10 Sep

Calgary (YYC)

to

Chicago (ORD)

C$545

roundtrip

found 6 days ago

Open YYC to ORD flights search result page

Carrier Flight Depart YYC Arrive ORD Sun
20/01		 Mon
21/01		 Tue
22/01		 Wed
23/01		 Thu
24/01		 Fri
25/01		 Sat
26/01		 Stops
UA 5877 00:33 pm 05:10 pm Check fare Check fare Check fare Check fare Check fare Check fare Check fare 0 stop(s)
UA 5314 03:20 pm 07:57 pm Check fare Check fare Check fare Check fare Check fare Check fare Check fare 0 stop(s)

Hotels by Airports near

See all 370 properties in O'Hare Intl.
Hilton Chicago O'Hare Airport C$146
See details
 
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

Ohare International Airport, Chicago
     
    4.0
    of 5, from 3,716 reviews
    4.0 out of 5.0

    The only hotel on airport property, the Hilton Chicago O'Hare Airport is located 2 miles from the Donald E. Stephens Convention Center and the Rosemont Theatre, and 18 miles from downtown Chicago.

    Edward Hotel Chicago C$115
    See details
     
    Edward Hotel Chicago

    Edward Hotel Chicago

    6600 N. Mannheim Rd, Rosemont
       
      4.0
      of 5, from 2,350 reviews
      3.0 out of 5.0

      Situated near the airport, this spa hotel is 0.4 mi (0.6 km) from Allstate Arena and within 3 mi (5 km) of Rivers Casino and Donald E. Stephens Convention Center. Rosemont Theatre and MB Financial Park at Rosemont are also within 3 mi (5 km). Rosemont O'Hare Transfer Station is 11 minutes by foot.

      Hyatt Place Chicago/O'Hare Airport C$130
      See details
       
      Hyatt Place Chicago/O'Hare Airport

      Hyatt Place Chicago/O'Hare Airport

      6810 Mannheim Rd, Rosemont
         
        4.5
        of 5, from 1,594 reviews
        3.0 out of 5.0

        Situated near the airport, this hotel is within 2 mi (3 km) of Allstate Arena, Museum of Hummels, and Rivers Casino. Donald E. Stephens Convention Center and Rosemont Theatre are also within 3 mi (5 km). Rosemont O'Hare Transfer Station is 13 minutes by foot.

        Loews Chicago O'Hare Hotel C$171
        See details
         
        Loews Chicago O'Hare Hotel

        Loews Chicago O'Hare Hotel

        5300 N River Rd, Rosemont
           
          4.5
          of 5, from 2,359 reviews
          4.5 out of 5.0

          This family-friendly Rosemont hotel is located near the airport, 3 mi (4.8 km) from Allstate Arena, and within 9 mi (15 km) of Stevenson Park and Portage Park. Hanson Park and Cernan Earth and Space Center are also within 9 mi (15 km). Rosemont Station is 20 minutes by foot and Rosemont Station is 15 minutes.

          Best Western At O'Hare C$103
          See details
           
          Best Western At O'Hare

          Best Western At O'Hare

          10300 W Higgins Road, Rosemont
             
            3.9
            of 5, from 1,013 reviews
            3.0 out of 5.0

            This hotel is 4 blocks from Allstate Arena (DePaul Blue Demons; Chicago Wolves) and 2 miles from O'Hare Airport; complimentary 24-hour shuttle service is provided.

            Crowne Plaza Hotel Chicago O'Hare C$118
            See details
             
            Crowne Plaza Hotel Chicago O'Hare

            Crowne Plaza Hotel Chicago O'Hare

            5440 N River Rd, Rosemont
               
              4.1
              of 5, from 2,066 reviews
              3.5 out of 5.0

              Situated near the airport, this hotel is 1.5 mi (2.3 km) from Rivers Casino and 2.7 mi (4.4 km) from Allstate Arena. Cernan Earth and Space Center and McDonald's Museum are also within 6 mi (10 km). Rosemont Station is 14 minutes by foot and Rosemont Station is 13 minutes.

              Wyndham Chicago O'Hare C$139
              See details
               
              Wyndham Chicago O'Hare

              Wyndham Chicago O'Hare

              1450 E Touhy Ave, Des Plaines
                 
                4.0
                of 5, from 2,197 reviews
                3.0 out of 5.0

                Complimentary shuttle service whisks guests arriving from O'Hare International to Wyndham Chicago O'Hare, a mere 2 miles away; concert-goers and hockey fans can stroll a block down to Allstate Arena.

                Aloft Chicago O'Hare C$142
                See details
                 
                Aloft Chicago O'Hare

                Aloft Chicago O'Hare

                9700 Balmoral Ave, Rosemont
                   
                  4.1
                  of 5, from 614 reviews
                  3.0 out of 5.0

                  Situated in Rosemont, this hotel is within a 5-minute walk of MB Financial Park at Rosemont and Rosemont Theatre. Catherine Chevalier Woods and Donald E. Stephens Convention Center are also within 10 minutes. Rosemont Station is 8 minutes by foot and Rosemont Station is 19 minutes.

                  See all 370 properties in O'Hare Intl.

                  Chicago

                  MDW-Midway Intl.

                  C$396.74

                  Top Routes from Calgary

                  Top Routes to Chicago

                  Cheap YYC to ORD Flights

                  • Question : What is the cheapest date to fly to Chicago?
                    Answer : As of Jan 14th, the best day for deals to Chicago (ORD) is Feb 12th. A ticket for this flight will run you around $357, which is 47% below this route's average price.
                  • Question : What is the cheapest airline flying from Calgary to Chicago?
                    Answer : Air Canada is your best flying friend for finding that sought-after low fare. They offer fares as low as $325, while prices for similar flights can cost as much as $1,426.
                  • Question : Which airline has the least delays from Calgary to Chicago?
                    Answer : Booking with Lufthansa means you will arrive to Chicago around the time you were supposed to. In fact, this airline has a 100% average for getting there on time. It never hurts to be prepared. If you should choose this airline, be sure to track the flight status to stay on top of the departure time.
                  • Question : How much time do people spend in Chicago?
                    Answer : The average time spent in Chicago by travellers from Calgary is about one week. However long you decide to stay, give yourself plenty of time to see what makes Chicago fantastic.
                  • Question : What is the cheapest day to fly?
                    Answer : The cheapest day to fly from Calgary to Chicago is on Friday. So, if you would like to save a bit of cash on your next business trip look for flights on that day.
                  • Question : How many flights are there per day from Calgary to Chicago?
                    Answer : The number of flight times varies by day, but on average, YYC to ORD sees five different options. Compared to the average route departing Canada with six flight times, you'll have fewer options.
                  • Question : How much is a plane ticket to Chicago (ORD) from Calgary (YYC)? They vary from $325 to $1,426. Booking far in advance can typically help you get the cheapest rate. Remember, booking ahead can save you dollars can use to treat yourself while on your holiday. And who doesn't like to treat themselves?
                    Answer : They vary from $325 to $1,426. Booking far in advance can typically help you get the cheapest rate. Remember, booking ahead can save you dollars can use to treat yourself while on your holiday. And who doesn't like to treat themselves?