C$ 116 Cheap Direct Flights to Chicago

Search hundreds of travel sites at once for deals on direct flights to Chicago

...and more

Travellers love KAYAK

41,299,237 searches in the past 7 days on KAYAK

Save 27% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flights Deals

Cheap Direct Flight Deals to Chicago

Here are some of the best deals found on KAYAK recently from the most popular airlines for direct round-trip flights to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.

Discover the best prices for you by selecting your travel dates on KAYAK.

4:05 p.m. - 4:54 p.m.YTZ-MDW

1h 49mdirect

5:20 p.m. - 8:02 p.m.MDW-YTZ

1h 42mdirect

C$ 180Porter Airlines

Find Deal

Wed, 25 Jun - Wed, 2 Jul

7:30 a.m. - 8:19 a.m.YTZ-MDW

1h 49mdirect

9:15 a.m. - 11:57 a.m.MDW-YTZ

1h 42mdirect

C$ 192Porter Airlines

Find Deal

Mon, 1 Sep - Fri, 5 Sep

12:15 p.m. - 4:44 p.m.YYC-ORD

3h 29mdirect

5:30 p.m. - 8:19 p.m.ORD-YYC

3h 49mdirect

C$ 264WestJet

Find Deal

Tue, 10 Jun - Tue, 24 Jun

2:10 p.m. - 3:05 p.m.YYZ-ORD

1h 55mdirect

8:25 p.m. - 11:07 p.m.ORD-YYZ

1h 42mdirect

C$ 266Air Canada

Find Deal

Fri, 30 May - Sat, 31 May

7:55 a.m. - 8:50 a.m.YYZ-ORD

1h 55mdirect

9:14 p.m. - 11:58 p.m.ORD-YYZ

1h 44mdirect

C$ 269Air Canada

Find Deal

Fri, 23 May - Mon, 26 May

12:15 p.m. - 4:44 p.m.YYC-ORD

3h 29mdirect

5:30 p.m. - 8:19 p.m.ORD-YYC

3h 49mdirect

C$ 270WestJet

Find Deal

Tue, 10 Jun - Tue, 24 Jun

6:29 a.m. - 10:54 a.m.YYC-ORD

3h 25mdirect

8:25 p.m. - 11:29 p.m.ORD-YYC

4h 04mdirect

C$ 309American Airlines

Find Deal

Wed, 2 Jul - Sun, 6 Jul

6:29 a.m. - 10:54 a.m.YYC-ORD

3h 25mdirect

8:30 p.m. - 11:29 p.m.ORD-YYC

3h 59mdirect

C$ 313American Airlines

Find Deal

Sat, 7 Jun - Mon, 9 Jun

6:15 a.m. - 7:59 a.m.YUL-ORD

2h 44mdirect

2:07 p.m. - 5:26 p.m.ORD-YUL

2h 19mdirect

C$ 349United Airlines

Find Deal

Fri, 23 May - Tue, 27 May

9:45 a.m. - 11:24 a.m.YUL-ORD

2h 39mdirect

10:40 a.m. - 1:58 p.m.ORD-YUL

2h 18mdirect

C$ 374United Airlines

Find Deal

Wed, 11 Jun - Wed, 9 Jul

Useful Info

KAYAK's insights & trends for direct flights to Chicago

Get data-powered insights and trends into direct flights to Chicago to help you find the cheapest direct flights, the best time to fly and much more.

Prices

Airlines