American Airlines

AAL4499 / AA4499

ICAO: AAL4499 IATA: AA4499

Click here to see all flights

Flight schedule

Select flight date

Departure

Arrive

Aircraft

Effective

Avalibility

09:08

Portland (PWM)

11:07

Chicago (ORD) T3

Embraer 175

Begins

2026-08-05

Valid to

2026-09-08

sun

mon

tue

wed

thu

fri

sat

Every day of the week except Saturdays

American Airlines

AAL4499

Duration

2h 59m

Distance

902 mi, 1451 km

Coreshare

Same day flight

Yes

Terminal

Arrival: T3

Meals

Onboard services

Wi-Fi

Seats

First class

Economy

06:46

Portland (PWM)

09:00

Chicago (ORD) T3

Embraer 175

Begins

2026-08-08

Valid to

2026-09-05

sun

mon

tue

wed

thu

fri

sat

Every Saturday

American Airlines

AAL4499

Duration

3h 14m

Distance

902 mi, 1451 km

Coreshare

Same day flight

Yes

Terminal

Arrival: T3

Meals

Onboard services

Wi-Fi

Seats

First class

Economy

06:30

Portland (PWM)

08:38

Chicago (ORD) T3

Embraer 175

Begins

2026-09-09

Valid to

2026-10-04

sun

mon

tue

wed

thu

fri

sat

Every weekday

American Airlines

AAL4499

Duration

3h 08m

Distance

902 mi, 1451 km

Coreshare

Same day flight

Yes

Terminal

Arrival: T3

Meals

Onboard services

Wi-Fi

Seats

First class

Economy

07:14

Portland (PWM)

09:10

Chicago (ORD) T3

Embraer 175

Begins

2026-10-05

Valid to

2026-10-31

sun

mon

tue

wed

thu

fri

sat

Every weekday

American Airlines

AAL4499

Duration

2h 56m

Distance

902 mi, 1451 km

Coreshare

Same day flight

Yes

Terminal

Arrival: T3

Meals

Onboard services

Wi-Fi

Seats

First class

Economy

10:10

Boston (BOS) TB

11:25

New York (LGA) TB

Embraer 175

Begins

2026-11-01

Valid to

2026-12-01

sun

mon

tue

wed

thu

fri

sat

Every weekday

American Airlines

AAL4499

Duration

1h 15m

Distance

185 mi, 298 km

Coreshare

Same day flight

Yes

Terminal

Departure: TB Arrival: TB

Meals

Onboard services

Wi-Fi

Seats

First class

Economy

10:09

Boston (BOS) TB

11:30

New York (LGA) TB

Embraer 175

Begins

2026-12-02

Valid to

2026-12-16

sun

mon

tue

wed

thu

fri

sat

Every weekday

American Airlines

AAL4499

Duration

1h 21m

Distance

185 mi, 298 km

Coreshare

Same day flight

Yes

Terminal

Departure: TB Arrival: TB

Meals

Onboard services

Wi-Fi

Seats

First class

Economy

11:00

Boston (BOS) TB

12:24

New York (LGA) TB

Embraer 170

Begins

2027-01-06

Valid to

2027-02-10

sun

mon

tue

wed

thu

fri

sat

Every weekday

American Airlines

AAL4499

Duration

1h 24m

Distance

185 mi, 298 km

Coreshare

Same day flight

Yes

Terminal

Departure: TB Arrival: TB

Meals

Onboard services

Wi-Fi

Seats

First class

Economy

08:45

New York (LGA) TB

10:01

Boston (BOS) TB

Embraer 170

Begins

2027-01-06

Valid to

2027-02-10

sun

mon

tue

wed

thu

fri

sat

Every weekday

American Airlines

AAL4499

Duration

1h 16m

Distance

185 mi, 298 km

Coreshare

Same day flight

Yes

Terminal

Departure: TB Arrival: TB

Meals

Onboard services

Wi-Fi

Seats

First class

Economy

11:00

Boston (BOS) TB

12:26

New York (LGA) TB

Embraer 170

Begins

2027-02-11

Valid to

2027-03-03

sun

mon

tue

wed

thu

fri

sat

Every weekday

American Airlines

AAL4499

Duration

1h 26m

Distance

185 mi, 298 km

Coreshare

Same day flight

Yes

Terminal

Departure: TB Arrival: TB

Meals

Onboard services

Wi-Fi

Seats

First class

Economy

08:45

New York (LGA) TB

10:03

Boston (BOS) TB

Embraer 170

Begins

2027-02-11

Valid to

2027-03-03

sun

mon

tue

wed

thu

fri

sat

Every weekday

American Airlines

AAL4499

Duration

1h 18m

Distance

185 mi, 298 km

Coreshare

Same day flight

Yes

Terminal

Departure: TB Arrival: TB

Meals

Onboard services

Wi-Fi

Seats

First class

Economy

11:00

Boston (BOS) TB

12:22

New York (LGA) TB

Embraer 170

Begins

2027-03-04

Valid to

2027-03-13

sun

mon

tue

wed

thu

fri

sat

Every weekday

American Airlines

AAL4499

Duration

1h 22m

Distance

185 mi, 298 km

Coreshare

Same day flight

Yes

Terminal

Departure: TB Arrival: TB

Meals

Onboard services

Wi-Fi

Seats

First class

Economy

08:45

New York (LGA) TB

10:00

Boston (BOS) TB

Embraer 170

Begins

2027-03-04

Valid to

2027-03-13

sun

mon

tue

wed

thu

fri

sat

Every weekday

American Airlines

AAL4499

Duration

1h 15m

Distance

185 mi, 298 km

Coreshare

Same day flight

Yes

Terminal

Departure: TB Arrival: TB

Meals

Onboard services

Wi-Fi

Seats

First class

Economy

11:00

Boston (BOS) TB

12:22

New York (LGA) TB

Embraer 170

Begins

2027-03-14

Valid to

2027-04-05

sun

mon

tue

wed

thu

fri

sat

Every weekday

American Airlines

AAL4499

Duration

1h 22m

Distance

185 mi, 298 km

Coreshare

Same day flight

Yes

Terminal

Departure: TB Arrival: TB

Meals

Onboard services

Wi-Fi

Seats

First class

Economy

08:45

New York (LGA) TB

10:00

Boston (BOS) TB

Embraer 170

Begins

2027-03-14

Valid to

2027-04-05

sun

mon

tue

wed

thu

fri

sat

Every weekday

American Airlines

AAL4499

Duration

1h 15m

Distance

185 mi, 298 km

Coreshare

Same day flight

Yes

Terminal

Departure: TB Arrival: TB

Meals

Onboard services

Wi-Fi

Seats

First class

Economy

19:35

Raleigh/Durham (RDU) T2

21:29

New York (LGA) TB

Embraer 175

Begins

2027-04-06

Valid to

2027-05-26

sun

mon

tue

wed

thu

fri

sat

Every weekday

American Airlines

AAL4499

Duration

1h 54m

Distance

432 mi, 695 km

Coreshare

Same day flight

Yes

Terminal

Departure: T2 Arrival: TB

Meals

Onboard services

Wi-Fi

Seats

First class

Economy

20:11

Raleigh/Durham (RDU) T2

22:05

New York (LGA) TB

Embraer 175

Begins

2027-05-27

Valid to

2027-06-01

sun

mon

tue

wed

thu

fri

sat

Every weekday

American Airlines

AAL4499

Duration

1h 54m

Distance

432 mi, 695 km

Coreshare

Same day flight

Yes

Terminal

Departure: T2 Arrival: TB

Meals

Onboard services

Wi-Fi

Seats

First class

Economy

According to schedule

Live tracker

PWM

Portland, US

left TERMINAL N/A

Portland - PWM

WEDNESDAY 03-JUN-2026

09:08 GMT-0400

ORD

Chicago, US

arrives TERMINAL 3

Chicago - ORD

WEDNESDAY 03-JUN-2026

11:07 GMT-0500

General route info

Frequency:

Daily

Sun Mon Tue Wed Thu Fri Sat

Direct distance

184 miles, 296 km

Actual distance

185 miles, 298 km

0.54%

Flight time

1h 15m

Flights / Week

28 flights

Seats / Week

75 seats/flight

2100 seats/week

Upcoming scheduled flights in the coming 30 days

Date

Time

From

To

Aircraft

Status

AAL4499 information

A domestic route in USA departing from Boston (BOS) and arriving at New York (LGA).

The timezones of the departure and arrival airports are identical, UTC -4.

The flight distance is 185 miles, or 298 km.

For direct flights, the flight time is about 1:15.

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Departure

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Other flights between Portland and Chicago with American Airlines

Popular Airports

Popular Airlines

American Airlines

AAL4499 / AA4499

Flight schedule

General route info

Frequency:

Direct distance

Actual distance

Flight time

Flights / Week

Seats / Week

Upcoming scheduled flights in the coming 30 days

AAL4499 information

Portland (PWM) Flight Deals

Portland Hotel Deals

Portland (PWM) Rental Cars

Portland (PWM) Parking

Other flights between Portland and Chicago with American Airlines

Popular Airports

Popular Airlines

American Airlines

AAL4499 / AA4499

Flight schedule

General route info

Frequency:

Direct distance

Actual distance

Flight time

Flights / Week

Seats / Week

Upcoming scheduled flights in the coming 30 days

AAL4499 information

Portland (PWM) Flight Deals

Portland Hotel Deals

Portland (PWM) Rental Cars

Portland (PWM) Parking

Select Destination Airport

Select Departure Airport

Other flights between Portland and Chicago with American Airlines

Portland (PWM) Flight Deals

Portland Hotel Deals

Portland (PWM) Rental Cars

Portland (PWM) Parking

Select Destination Airport

Select Departure Airport