Cheap flights from Chicago to South Portland

Chicago FSS
CHI
Portland
PWM

Flight deals from Chicago to South Portland

Below you can see the best deals on flights Chicago — South Portland 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 19 October, from $101.

Top 10 cheap flights from Chicago to South Portland

DL
DL
DL
$ 150

Chicago — South Portland

13:55—23:17
22 Sep 2026
8 h 22 m
2 stops
DL
DL
DL
$ 150

Chicago — South Portland

13:19—23:17
22 Sep 2026
8 h 58 m
2 stops
DL
DL
DL
$ 150

Chicago — South Portland

13:51—23:17
22 Sep 2026
8 h 26 m
2 stops
DL
DL
DL
$ 150

Chicago — South Portland

13:55—23:56
22 Sep 2026
9 h 1 m
2 stops
DL
DL
DL
$ 150

Chicago — South Portland

13:55—23:28
22 Sep 2026
8 h 33 m
2 stops
DL
DL
DL
$ 152

Chicago — South Portland

13:55—23:17
16 Sep 2026
8 h 22 m
2 stops
DL
DL
DL
$ 152

Chicago — South Portland

13:19—23:17
16 Sep 2026
8 h 58 m
2 stops
DL
DL
DL
$ 152

Chicago — South Portland

13:55—23:56
16 Sep 2026
9 h 1 m
2 stops
DL
DL
DL
$ 152

Chicago — South Portland

06:10—16:01
19 Sep 2026
8 h 51 m
2 stops
DL
DL
DL
$ 152

Chicago — South Portland

07:05—15:39
15 Sep 2026
7 h 34 m
2 stops

Prices were found in the last 72 hours and may change — check the exact price when you continue.

About the Chicago — South Portland flight

Looking for cheap flights from Chicago to South Portland? Compare fares from different airlines, check the flight schedule and travel time — and book your Chicago — South Portland ticket online at the best price.

The route has direct flights — around 63 flights per week, flights are operated by American Airlines, United Airlines, a nonstop flight takes about 2 h 31 min, the distance between the cities is around 1,434 km.

Planning your trip? You may find our South Portland travel guide, how to get from the airport into town and South Portland weather forecast useful. To catch a low fare, use the low-price calendar and the monthly price chart on this page.

Facts about this route

from $101Min. price
OctoberCheapest
AprilPeak season
YesDirect flights
1,434 kmDistance
2 h 31 minTravel time
2Airlines
63 / wkFlights

Flight schedule from Chicago to South Portland

The table shows direct flights from Chicago to South Portland on the selected date. The flight takes approximately 2 h 31 min. Regular flights are operated by American Airlines and United Airlines. Departures from O'Hare International Airport, Chicago Midway International Airport and Midway International Airport airports, arrivals at Portland International Jetport.

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.

Today
Any time
Last update: 25 Aug 2026

Flight ticket prices by day: Chicago — 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 $101 in October, and the most expensive are around $209 in April. 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

Average one-way fares from Chicago to South Portland by month. Tickets are usually cheapest in February (around $174) and priciest in July (about $234) — use the table and chart below to pick the best time to fly.

MonthAverage priceLevelMonthAverage priceLevelMonthAverage priceLevel
Jan$192mediumMay$198mediumSep$192medium
Feb$174lowJun$222highOct$228high
Mar$174lowJul$234highNov$186medium
Apr$180lowAug$222highDec$210high

Some values are estimated based on seasonality.

When to fly

Weather in South Portland: it is warmest in July (up to 25 °C on average) and coolest in January (around 1 °C). The driest month is September.

Tickets are usually cheapest in October and most expensive in April. Compare prices and weather by month in the charts below to pick the best time to fly.

Temperature · South Portland

Dry and wet days · South Portland

Wind speed and direction · South Portland

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

  • Book ahead: fares for Chicago — South Portland are usually lower 3–8 weeks before departure than at the last minute.
  • Play with your dates — Tuesday, Wednesday and Saturday departures are often cheaper than Friday and Sunday.
  • Chicago is served by more than one airport — compare fares and travel time to each before you book.
  • The cheapest month to fly to South Portland is usually October — plan your trip around it if your dates are flexible.
  • Compare direct and connecting flights: nonstop is faster, while a connection is sometimes noticeably cheaper.
  • Watch the low-price calendar and the monthly price trend on this page — they make it easier to catch a good date.
  • Travelling light? Pick a cabin-baggage-only fare — tickets without checked luggage are noticeably cheaper.
  • Get to the airport in good time — about 2–3 hours before an international departure and roughly an hour before a domestic one.

Airlines

Flights on the Chicago — South Portland route are operated by 2 airlines; American Airlines runs the most flights (around 56% of all flights). Compare carriers, flight shares and schedules below.

  • American AirlinesAA
    12x/week
    WebsiteFleet: 965211M pax/year
    • Direct flight ORD → PWM12x/week
      Duration
      2h 32m
      Days
      MTWTFSS
    55.6%Open →
  • United AirlinesUA
    9x/week
    WebsiteFleet: 956165M pax/year
    • Direct flight ORD → PWM9x/week
      Duration
      2h 35m
      Days
      MTWTFSS
    44.4%Open →

Cities and airports on the Chicago — South Portland route

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.

Departure

Chicago

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

South Portland

PWM
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 Chicago — South Portland flight

How long is the flight from Chicago to South Portland?

A nonstop Chicago — South Portland flight takes about 2 h 31 min — the distance between the cities is around 1,434 km.

How far is it from Chicago to South Portland?

The distance from Chicago to South Portland is about 1,434 km, which a nonstop flight covers in around 2 h 31 min.

Are there direct flights from Chicago to South Portland?

Yes, there are nonstop flights Chicago — South Portland — around 63 flights per week.

Which airlines fly from Chicago to South Portland?

Airlines operating Chicago — South Portland include American Airlines, United Airlines. See the full list with schedules in the "Airlines" section on this page.

Which airports do Chicago — South Portland flights use?

Flights from Chicago depart from O'Hare International Airport, Chicago Midway International Airport, Midway International Airport, and arrive at Portland International Jetport. If a city has more than one airport, check which one your ticket uses before you travel.

How much is a ticket from Chicago to South Portland?

The price of a Chicago — South Portland ticket depends on your travel date, season and demand: it is usually cheapest to fly in October, and most expensive in April. Tickets typically cost between $101 and $209. Check the current lowest fare and low-price calendar on this page.

When is the best time to book flights Chicago — South Portland?

Flights Chicago — South Portland are usually cheaper when booked in advance — a few weeks before departure and away from peak dates; the most budget-friendly month to fly is October. Compare prices by month in the price trend chart on this page.

How can I find the cheapest flights from Chicago to South Portland?

To catch a low fare Chicago — South Portland, book a few weeks in advance, keep your dates flexible, and compare airlines and connecting options. The low-price calendar and monthly price chart on this page show the cheapest days and months at a glance: the most budget-friendly month to fly is usually October.

How early should I arrive at the airport?

For international flights, plan to be at the airport about 2–3 hours before departure, and around an hour before a domestic flight. Allow extra time during busy travel seasons and at large hubs, where check-in and security lines can be longer.

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Where else you can fly from South Portland

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New York CityWashington, D.C.PhiladelphiaAtlantaCharlotteDetroitDenverMinneapolisDallasOrlandoHoustonTampaLos AngelesSan FranciscoSyracuse

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