On this page, you can find and book flights from Chicago to South Portland. The 1,434 km route is serviced regularly, with approximately 21 flights per week.
Flights on this route are operated by United Airlines and American Airlines. Ticket prices fluctuate based on demand, so we recommend using the low-fare calendar and price chart. Before your trip, check out the information on how to get to Chicago airport and how to get from the airport to South Portland.
Below is a calendar of the lowest flight ticket prices for Chicago — South Portland by day. Pick a convenient date and instantly see the fare. The cheapest flights on this route start from AED 387 in ,, and the most expensive are around AED 832 in u. 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.
Chicago → South Portland, average one-way price
| Month | Average price | Level | Month | Average price | Level | Month | Average price | Level |
|---|---|---|---|---|---|---|---|---|
| Jan | AED 770 | medium | May | AED 794 | medium | Sep | AED 770 | medium |
| Feb | AED 698 | low | Jun | AED 890 | high | Oct | AED 914 | high |
| Mar | AED 698 | low | Jul | AED 938 | high | Nov | AED 746 | medium |
| Apr | AED 722 | low | Aug | AED 890 | high | Dec | AED 842 | high |
Some values are estimated based on seasonality.
The warmest month in South Portland is July, when average temperatures reach 24.8°C. The coldest weather and highest humidity are observed in January and December, when temperatures drop to -5.8°C and precipitation levels reach their peak.
From a budget perspective, the most cost-effective time to fly is July, with fares starting AED 418. Prices peak in June, where the minimum fare starts AED 954, and in April with offers starting AED 832.
October is considered the optimal time for a trip: mild temperatures of around 15.3°C are paired with affordable flight prices starting AED 419. It is recommended to avoid booking for April due to the significant increase in ticket fares.
There are two main airlines operating on the route from Chicago to South Portland: United Airlines and American Airlines. Approximately 21 regular flights are operated per week, including direct flight options. You can view the detailed schedule for specific days and choose a convenient departure time in the interactive list below.
Flights Chicago — South Portland depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport and arrive at Portland International Jetport. Below are pages for the cities, countries, and airports on the route: airlines, schedules, and travel guides.
The estimated direct flight time is about 1 hour and 50 minutes, covering a distance of 1,434 km.
Regular air service between the cities is provided by United Airlines and American Airlines.
Yes, direct flights are available on this route, with a total of approximately 21 departures per week.
Flight prices change constantly depending on the season. You can see the current minimum for specific dates in the low-fare calendar on this page.
Flights from Chicago arrive at the South Portland airport (PWM), located in the state of Maine.
Where travelers fly most — pick a route and check prices
