How far in advance should I book tickets for a flight with United Airlines from Toronto to Chicago?

Generally, when trying to get a below-average price for your ticket, try to book around 14 days before departure. For the cheapest possible price, our data suggests booking 47 days before departure.

Is United Airlines the cheapest airline to fly with from Toronto to Chicago?

With an average price of C$ 392 return, United Airlines is not the cheapest airline to fly from Toronto to Chicago with. Instead, for the lowest price, our data suggests flying with Porter Airlines, where a return flight costs C$ 316 on average.

What is the cheapest United Airlines flight from Toronto to Chicago?

In the last 3 days, the lowest price for a flight with United Airlines from Toronto to Chicago was C$ 219 for a return flight and C$ 140 for a one-way flight.

Does United Airlines fly direct to Chicago from Toronto?

Yes, United Airlines does offer direct flights for the route, with around 48 flights per week.

What’s the cheapest day of the week to fly from Toronto to Chicago with United Airlines?

On average, the cheapest day of the week to fly from Toronto to Chicago with United Airlines is Wednesday, when prices are around C$ 164. The most expensive day is generally Sunday, when the average price is around C$ 194.

What’s the cheapest month to fly from Toronto to Chicago with United Airlines?

The cheapest month for United Airlines flights to Chicago from Toronto is generally October, where plane tickets cost C$ 217 on average. If possible, try to avoid the most expensive months of September and August, when tickets cost C$ 413 and C$ 557 respectively.

C$ 172 Cheap United Airlines Flights from Toronto to Chicago

Flight Deals

Cheap United Airlines Flight Deals from Toronto to Chicago

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Recent round-trip United Airlines flight deals from Toronto to Chicago

Fri, 27 Mar - Sun, 29 Mar

9:00 p.m. - 10:04 p.m.

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2h 04mdirect

9:15 p.m. - 11:59 p.m.

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1h 44mdirect

C$ 271United Airlines

Tue, 10 Mar - Sun, 15 Mar

9:00 p.m. - 10:04 p.m.

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2h 04mdirect

7:10 a.m. - 9:58 a.m.

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1h 48mdirect

C$ 283United Airlines

Sun, 5 Apr - Wed, 8 Apr

11:00 a.m. - 12:03 p.m.

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2h 03mdirect

10:52 a.m. - 1:42 p.m.

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1h 50mdirect

C$ 309United Airlines

Thu, 5 Mar - Sun, 8 Mar

6:45 a.m. - 8:00 a.m.

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2h 15mdirect

6:25 p.m. - 9:18 p.m.

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1h 53mdirect

C$ 310United Airlines

Tue, 12 May - Sat, 16 May

1:00 p.m. - 2:01 p.m.

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2h 01mdirect

9:15 p.m. - 11:59 p.m.

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1h 44mdirect

C$ 312United Airlines

Tue, 3 Mar - Thu, 5 Mar

9:00 p.m. - 10:04 p.m.

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2h 04mdirect

1:12 p.m. - 4:02 p.m.

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1h 50mdirect

C$ 321United Airlines

Thu, 5 Mar - Sun, 8 Mar

9:00 p.m. - 10:04 p.m.

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2h 04mdirect

6:25 p.m. - 9:18 p.m.

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1h 53mdirect

C$ 322United Airlines

Thu, 5 Mar - Sun, 8 Mar

6:45 a.m. - 8:00 a.m.

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2h 15mdirect

6:25 p.m. - 9:18 p.m.

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1h 53mdirect

C$ 324United Airlines

Fri, 15 May - Tue, 19 May

7:00 a.m. - 8:00 a.m.

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2h 00mdirect

1:01 p.m. - 3:46 p.m.

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1h 45mdirect

C$ 327United Airlines

Fri, 20 Mar - Wed, 25 Mar

5:30 p.m. - 6:40 p.m.

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2h 10mdirect

6:25 p.m. - 9:18 p.m.

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1h 53mdirect

C$ 328United Airlines

Useful Info

Low season	April
High season	October
Cheapest flight	C$ 172
Average price round-trip	C$ 383

Best time to beat the crowds (16% less expensive on average)

Most popular time to fly and prices are also 2% lower on average.

Flight from Toronto Pearson Airport to Chicago O'Hare Airport

(price for this month)

When to Book Flights with United Airlines from Toronto to Chicago

Average price per month

Flight prices as travel date approaches

How far in advance should I book tickets for a flight with United Airlines from Toronto to Chicago?
Generally, when trying to get a below-average price for your ticket, try to book around 14 days before departure. For the cheapest possible price, our data suggests booking 47 days before departure.
Is United Airlines the cheapest airline to fly with from Toronto to Chicago?
With an average price of C$ 392 return, United Airlines is not the cheapest airline to fly from Toronto to Chicago with. Instead, for the lowest price, our data suggests flying with Porter Airlines, where a return flight costs C$ 316 on average.
What is the cheapest United Airlines flight from Toronto to Chicago?
In the last 3 days, the lowest price for a flight with United Airlines from Toronto to Chicago was C$ 219 for a return flight and C$ 140 for a one-way flight.
Does United Airlines fly direct to Chicago from Toronto?
Yes, United Airlines does offer direct flights for the route, with around 48 flights per week.
What’s the cheapest day of the week to fly from Toronto to Chicago with United Airlines?
On average, the cheapest day of the week to fly from Toronto to Chicago with United Airlines is Wednesday, when prices are around C$ 164. The most expensive day is generally Sunday, when the average price is around C$ 194.
What’s the cheapest month to fly from Toronto to Chicago with United Airlines?
The cheapest month for United Airlines flights to Chicago from Toronto is generally October, where plane tickets cost C$ 217 on average. If possible, try to avoid the most expensive months of September and August, when tickets cost C$ 413 and C$ 557 respectively.

7.4

Good9,283 verified ratings

7.3Comfort

7.7Boarding

7.1Entertainment

8.1Crew

6.6Food

8.0 Very good

Verified traveller, Feb 2026

HND

LAX

Good. Did not feel like a 12 hour flight

10.0 Wonderful

Darnell, Feb 2026

DEN

CUN

Great experience flights arrived earlier than expected.

10.0 Wonderful

Darnell, Feb 2026

COS

DEN

Both of my flights arrived early and check in process was smooth

2.0 Poor

Verified traveller, Feb 2026

SFO

RDU

Terrible. No customer service, no food, no drinks on a 6 hour premier economy booking.

2.0 Poor

Verified traveller, Feb 2026

HKG

SFO

worst customer service I've ever experienced

2.0 Poor

Verified traveller, Feb 2026

BKK

HKG

Absolutely terrible. I booked my ticket with ANA and underpricer/kayak asked me to change all my return flights to United. Customer service does not exist with United. Flight attendants are rude, self-centered, and unhelpful. The food is served cold and uncovered. The in-flight video controllers do not work properly. Premier economy tickets with ANA, allow you access to all airport lounges, while United does not allow access to any lounge. Mockery of an airline.

6.0 Okay

Daymond, Feb 2026

ORD

SDF

Short flight, but no drink/snack service. The flights both going and coming were delayed.

10.0 Wonderful

Alissa, Feb 2026

EWR

TPA

Much better than Spirit. I was please by the easy fast check in and boarding

10.0 Wonderful

Stacy, Feb 2026

RDD

DEN

Made up time and smooth flight overall

6.0 Okay

James, Feb 2026

HND

IAD

Crew was great. 2 1/2 hour delay was due to staff needing "rest" was avoidable and self inflicted as United not willing to hire enough crew to keep flight on time.. Ridiculous. The crew and the passengers both suffered due to this.

Everything you need to know for your flight from Toronto to Chicago

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C$ 172 Find Cheap United Airlines Flights from Toronto to Chicago

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Cheap United Airlines Flight Deals from Toronto to Chicago

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Good to know

When to Book Flights with United Airlines from Toronto to Chicago

FAQs for flying to Chicago with United Airlines

How far in advance should I book tickets for a flight with United Airlines from Toronto to Chicago?

Generally, when trying to get a below-average price for your ticket, try to book around 14 days before departure. For the cheapest possible price, our data suggests booking 47 days before departure.

Is United Airlines the cheapest airline to fly with from Toronto to Chicago?

With an average price of C$ 392 return, United Airlines is not the cheapest airline to fly from Toronto to Chicago with. Instead, for the lowest price, our data suggests flying with Porter Airlines, where a return flight costs C$ 316 on average.

What is the cheapest United Airlines flight from Toronto to Chicago?

In the last 3 days, the lowest price for a flight with United Airlines from Toronto to Chicago was C$ 219 for a return flight and C$ 140 for a one-way flight.

Does United Airlines fly direct to Chicago from Toronto?

Yes, United Airlines does offer direct flights for the route, with around 48 flights per week.

What’s the cheapest day of the week to fly from Toronto to Chicago with United Airlines?

On average, the cheapest day of the week to fly from Toronto to Chicago with United Airlines is Wednesday, when prices are around C$ 164. The most expensive day is generally Sunday, when the average price is around C$ 194.

What’s the cheapest month to fly from Toronto to Chicago with United Airlines?

The cheapest month for United Airlines flights to Chicago from Toronto is generally October, where plane tickets cost C$ 217 on average. If possible, try to avoid the most expensive months of September and August, when tickets cost C$ 413 and C$ 557 respectively.

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Everything you need to know for your flight from Toronto to Chicago

Other airlines flying from Toronto to Chicago

Flights from the other most popular airlines that fly from Toronto to Chicago according to KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.

Cabin class types available on flights from Toronto to Chicago

Cabin classes available on flights from Toronto to Chicago. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.

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The most popular flights on KAYAK according to clicks in the last 2 weeks. Prices are the lowest found on KAYAK over the last 7 days. Price and availability are not guaranteed.

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Top United Airlines flights

The most popular destinations for flights with United Airlines according to clicks from KAYAK users. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.