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Direct flights to Chicago from C$ 171

This is the cheapest price on a non-stop flight to Chicago found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/7. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
16 jun. — 23 jun.1
1 adult
dom. 16/6
dom. 23/6

Cheap direct flight deals to Chicago

Discover affordable direct flight deals to Chicago. In the last 7 days, Cheapflights users made a total of 442,058 searches and data was last updated on 11 junio 2024.
mar. 16/79:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
dom. 21/78:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/6C$ 286
jue. 11/77:00 a.m.YYZ - ORD
Nonstop1h 57mAir Canada
jue. 11/79:15 p.m.ORD - YYZ
Nonstop1h 43mAir Canada
Deal found 11/6C$ 319
jue. 5/97:00 a.m.YYZ - ORD
Nonstop1h 56mUnited Airlines
lun. 9/97:26 a.m.ORD - YYZ
Nonstop1h 32mUnited Airlines
Deal found 11/6C$ 321
vie. 16/89:00 p.m.YYZ - ORD
Nonstop2h 02mMultiple Airlines
dom. 18/86:00 a.m.ORD - YYZ
Nonstop1h 48mMultiple Airlines
Deal found 10/6C$ 339
lun. 1/71:20 p.m.YYZ - ORD
Nonstop1h 55mAmerican Airlines
mar. 2/711:54 a.m.ORD - YYZ
Nonstop1h 35mAmerican Airlines
Deal found 10/6C$ 346
jue. 4/73:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
dom. 7/78:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/6C$ 288
vie. 5/78:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
dom. 7/712:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/6C$ 289
mar. 17/98:05 a.m.YYZ - ORD
Nonstop1h 56mUnited Airlines
mar. 17/912:04 p.m.ORD - YYZ
Nonstop1h 48mUnited Airlines
Deal found 10/6C$ 322
lun. 16/97:50 p.m.YYZ - ORD
Nonstop1h 53mAir Canada
sáb. 21/97:26 a.m.ORD - YYZ
Nonstop1h 32mAir Canada
Deal found 10/6C$ 323

One-way direct flights to Chicago

Explore one-way non-stop flights to Chicago for greater flexibility in your travel plans. Find up-to-date pricing and availability for one-way flights. In the last 7 days, Cheapflights users made a total of 442,058 searches and data was last updated on 11 junio 2024.
lun. 8/79:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 11/6C$ 171
mar. 9/78:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 11/6C$ 172
mar. 2/79:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 10/6C$ 173
dom. 4/810:30 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 11/6C$ 176
mar. 13/88:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 10/6C$ 178
mar. 9/73:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 11/6C$ 180
mié. 26/68:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 10/6C$ 182
dom. 4/88:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 10/6C$ 183
mié. 3/78:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
Deal found 10/6C$ 184

Round-trip direct flights to Chicago

Explore round-trip direct flights to Chicago. Find up-to-date pricing and availability for round-trip flights. In the last 7 days, Cheapflights users made a total of 442,058 searches and data was last updated on 11 junio 2024.
mar. 16/79:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
dom. 21/78:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/6C$ 286
jue. 4/73:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
dom. 7/78:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/6C$ 288
vie. 5/78:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
dom. 7/712:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/6C$ 289
vie. 9/88:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 24/88:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/6C$ 293
vie. 9/88:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 24/88:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/6C$ 295
sáb. 27/710:45 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 17/88:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/6C$ 296
mié. 26/68:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
dom. 30/65:25 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/6C$ 297
mar. 23/79:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 27/78:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/6C$ 299
mié. 7/88:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
sáb. 24/812:30 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/6C$ 300

Direct flights to Chicago departing soon

Discover non-stop flights to Chicago departing soon. In the last 7 days, Cheapflights users made a total of 442,058 searches and data was last updated on 11 junio 2024.
vie. 21/68:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
dom. 23/68:40 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 9/6C$ 372
mar. 18/69:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
mié. 26/68:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/6C$ 383
vie. 21/68:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
lun. 24/68:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/6C$ 388
lun. 17/69:20 a.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
lun. 24/611:25 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/6C$ 398
mié. 19/63:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
mié. 26/68:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 10/6C$ 399
mar. 18/63:30 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
vie. 28/68:00 a.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/6C$ 405
mar. 18/69:00 a.m.YYZ - ORD
Nonstop1h 54mAir Canada
mié. 26/66:00 a.m.ORD - YYZ
Nonstop1h 48mAir Canada
Deal found 11/6C$ 410
mar. 18/67:55 a.m.YYZ - ORD
Nonstop1h 56mAir Canada
dom. 30/66:00 a.m.ORD - YYZ
Nonstop1h 48mAir Canada
Deal found 9/6C$ 413
vie. 21/68:50 p.m.YTZ - MDW
Nonstop1h 47mPorter Airlines
dom. 23/612:15 p.m.MDW - YTZ
Nonstop1h 42mPorter Airlines
Deal found 11/6C$ 436

Best time to book a flight to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Find direct flights to Chicago within your budget

Use the slider to find non-stop flights to Chicago within your budget. Price data is based on user searches made on Cheapflights. Over the past seven days, Cheapflights users made 442,058 searches and data was last updated on 11 junio 2024.

Fly from

Any airport

Budget

C$ 286 - C$ 346

Route

Depart

Return

Price

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

mar. 16/7

Nonstop1h 47m

Chicago Midway

dom. 21/7

Nonstop1h 42m

C$ 286

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

jue. 4/7

Nonstop1h 47m

Chicago Midway

dom. 7/7

Nonstop1h 42m

C$ 288

Toronto IslandChicago Midway

YTZ - MDW

YTZMDW

Toronto Island

vie. 5/7

Nonstop1h 47m

Chicago Midway

dom. 7/7

Nonstop1h 42m

C$ 289

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

jue. 11/7

Nonstop1h 57m

Chicago O'Hare Intl

jue. 11/7

Nonstop1h 43m

C$ 319

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

jue. 5/9

Nonstop1h 56m

Chicago O'Hare Intl

lun. 9/9

Nonstop1h 32m

C$ 321

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

mar. 17/9

Nonstop1h 56m

Chicago O'Hare Intl

mar. 17/9

Nonstop1h 48m

C$ 322

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

lun. 16/9

Nonstop1h 53m

Chicago O'Hare Intl

sáb. 21/9

Nonstop1h 32m

C$ 323

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

vie. 16/8

Nonstop2h 02m

Chicago O'Hare Intl

dom. 18/8

Nonstop1h 48m

C$ 339

Toronto Pearson IntlChicago O'Hare Intl

YYZ - ORD

YYZORD

Toronto Pearson Intl

lun. 1/7

Nonstop1h 55m

Chicago O'Hare Intl

mar. 2/7

Nonstop1h 35m

C$ 346

Flights are sorted by cheapest first

Deals found on 10/6

Reviews of airlines flying non-stop to Chicago

Get insights into the airlines that provide direct flights to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 11 junio 2024.
8.0
Very good
10,277 reviews

Boarding

8.2

Crew

8.6

Comfort

7.9

Entertainment

8.0

Food

7.4

Overall

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

8.0
Very good
10,277 reviews
8.0
Very good
10,277 reviews

Boarding

8.2

Crew

8.6

Comfort

7.9

Entertainment

8.0

Food

7.4

Overall

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

7.5
Good
380 reviews
8.0
Very good
10,277 reviews

Boarding

8.2

Crew

8.6

Comfort

7.9

Entertainment

8.0

Food

7.4

Overall

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

7.5
Good
2,842 reviews
8.0
Very good
10,277 reviews

Boarding

8.2

Crew

8.6

Comfort

7.9

Entertainment

8.0

Food

7.4

Overall

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

7.4
Good
10,629 reviews
8.0
Very good
10,277 reviews

Boarding

8.2

Crew

8.6

Comfort

7.9

Entertainment

8.0

Food

7.4

Overall

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

7.3
Good
14,129 reviews
8.0
Very good
10,277 reviews

Boarding

8.2

Crew

8.6

Comfort

7.9

Entertainment

8.0

Food

7.4

Overall

8.0

Reviews

1 / 10

When I was going to board, one of the staff members told me that I could not board with my passport bag because it was tree items and I would need to check a bag. This was so stupid ! The bag was small. So I had to put my things in my pockets, put the funny bag inside the other bag. Then go throw it. Then in the plane put everything back again in my funny bag.

Temperature and rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average temperature and rainfall totals by month.

CHI

Temperature

-5 - 23 °C

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

FAQ about direct flights to Chicago

Find answers to frequently asked questions about direct flights to Chicago to unlock the best deals on Cheapflights.
  • How much are direct flights to Chicago?

    On average, a one-way direct flight to Chicago will cost users approximately C$ 465. If you're looking for a direct round-trip flight to Chicago, you can expect to pay around C$ 1,115.

  • What is the best time of year to fly direct to Chicago?

    If you're seeking the lowest price on a direct flight to Chicago, January is worth consideration, as prices are usually at their lowest, on average. January may be most appealing to users looking for the quietest time to visit Chicago, when demand is typically at its lowest.

  • What is the most popular direct flight origin to Chicago?

    Currently, the most popular direct flight origin to Chicago is Toronto Pearson Intl Airport. A round-trip direct flight from Toronto Pearson Intl Airport to Chicago typically costs around C$ 1,268.

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