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Flights South Portland — Chicago

Portland
PWM
Chicago
CHI

Cheap flights South Portland — Chicago

Below you can see the best deals on flights South Portland — Chicago for upcoming dates. Direct and connecting flights from various airlines — compare prices and choose the right ticket.

The lowest price for the next 2 months is on 29 August, from AED 402.

Top 10 cheap flights South Portland — Chicago

Direct flights South Portland — Chicago

Direct flight options for South Portland — Chicago with no stopovers on upcoming dates. A direct flight is faster and more convenient — especially when travelling with luggage or children.

The fastest direct flight is operated by United Airlines — travel time is 3 h.

Top 10 direct flights South Portland — Chicago

About the South Portland — Chicago flight

On this page, you can find and purchase flight tickets for the South Portland — Chicago route. The flight covers a distance of 1,434 km, with a frequency of about 17 flights per week, making it easy to find a convenient departure time.

Regular air service is provided by UA and AA. Ticket prices change constantly, so we recommend using the price dynamics chart and calendar on our website to find the best deal. You can also find information on how to get to the airport in South Portland and how to reach the city center after arriving in Chicago.

Flight schedule South Portland — Chicago

The table shows direct flights South Portland → Chicago on the selected date. The flight takes approximately 3 h. Regular flights are operated by American Airlines and United Airlines. Departures from Portland International Jetport airports, arrivals at O'Hare International Airport, Chicago Midway International Airport and Midway International Airport.

For each flight, the following details are shown: departure time (local), arrival city and airport, flight number and airline, terminal or gate, and status. Click on a flight to open its details and go to ticket search. To view flights on a different day, change the date above the table.

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Flight ticket prices by day: South Portland — Chicago

Below is a calendar of the lowest flight ticket prices for South Portland — Chicago by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from AED 358 in F, and the most expensive are around AED 811 in J. If your travel dates are flexible, the calendar will help you find the best price for your preferred period. To view round-trip fares, switch to the "Round trip" tab above the calendar, select your departure date — and the right-hand calendar will highlight the lowest prices for return flights on each day.

 
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Prices by month

South Portland → Chicago, average one-way price

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
JanAED 700highMayAED 645mediumSepAED 571low
FebAED 645mediumJunAED 682highOctAED 626medium
MarAED 663mediumJulAED 682highNovAED 663high
AprAED 700highAugAED 590lowDecAED 682high

Some values are estimated based on seasonality.

When to fly

The warmest month in Chicago is July, with an average temperature of 26.5°C. The coldest weather and frequent precipitation occur in January, when temperatures drop to -5°C, while May is considered the rainiest time of the year.

The lowest flight price was recorded in September, starting AED 359. Prices peak in January, with tickets starting AED 814, making winter departures the least budget-friendly option.

September is the optimal choice for a trip, offering a comfortable 23.5°C and the lowest fares. We recommend avoiding January bookings due to the combination of high prices and unfavorable weather conditions.

Temperature · Chicago

Dry and wet days · Chicago

Wind speed and direction · Chicago

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How to get the best deal on a South Portland — Chicago ticket

  • Plan your ticket purchase to Chicago for September, when the lowest prices are recorded, starting AED 359.
  • Keep an eye on the low price calendar on this page, as mid-week departures are usually cheaper than weekend flights.
  • Keep in mind that for this 1,434 km route, UA and AA often offer direct flights, which saves time compared to connecting options.
  • Use the price dynamics chart to spot seasonal price drops in time and book your ticket at the most favorable rate.

Airlines

Two major airlines operate on this route — United Airlines (UA) and American Airlines (AA). A total of about 17 flights per week are operated, providing regular service between the cities. You can find detailed information on departure times, aircraft types, and specific days of the week in the schedule below: simply click on the card of the carrier you're interested in.

  • American Airlines
    American AirlinesAA
    11x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight PWM → ORD11x/week
      Duration
      3h 6m
      Days
      MTWTFSS
    63.5%Open →
  • United Airlines
    United AirlinesUA
    6x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight PWM → ORD6x/week
      Duration
      3h 4m
      Days
      MTWTFSS
    36.5%Open →

Cities and airports on the South Portland — Chicago route

Flights South Portland — Chicago depart from Portland International Jetport and arrive at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.

Departure

South Portland

PWM
United States
About the cityHow to get thereWeatherAll about the country United States
Arrival

Chicago

CHI
United States
About the cityHow to get thereWeatherAll about the country United States
Departure airports
Arrival airports

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Frequently asked questions about the South Portland — Chicago flight

How long is the flight from South Portland to Chicago?

The average direct flight time for the 1,434 km distance is about 1 hour 50 minutes. The exact duration depends on the specific flight and weather conditions.

Which airlines fly this route?

Regular flights from South Portland are operated by United Airlines (UA) and American Airlines (AA).

When is the best time to buy flight tickets?

The most affordable prices are found when booking in advance for September. You can always check the current minimum in the low price calendar on this page.

Which airport does the flight arrive at?

Flights from South Portland typically arrive at O'Hare International Airport in Chicago, which is one of the largest transportation hubs in the US.

Are there direct flights on this route?

Yes, airlines operate direct flights, which is the most convenient way to reach your destination without any layovers.

Where else you can fly from South Portland

New York CityWashington, D.C.PhiladelphiaAtlantaCharlotteDetroitDenverMinneapolisDallasOrlandoHoustonLos AngelesSan FranciscoTampa

Where else you can fly from Chicago

New York CityTorontoDetroitWashington, D.C.AtlantaMinneapolisLos AngelesSeattleBostonDallasHoustonOrlandoDenverNashvilleLondonIndianapolisSan DiegoMontrealMilwaukeeSt. LouisCharlottePhiladelphiaColumbusKansas CityMiamiPhoenixLas VegasCincinnatiGrand RapidsDes MoinesRaleighSan FranciscoMadisonDaytonGreen BayTampaPittsburghLouisvilleKnoxvilleRochester
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