What is the cheapest way to get from South Portland to Chicago?

The cheapest way to get from South Portland to Chicago is to bus which costs $150 - $280 and takes 30h 3m.

What is the fastest way to get from South Portland to Chicago?

The fastest way to get from South Portland to Chicago is to fly which takes 5h 34m and costs $130 - $750.

Is there a direct bus between South Portland and Chicago?

No, there is no direct bus from South Portland to Chicago station. However, there are services departing from Danforth St + High St and arriving at Chicago Bus Station via Congress St + Forest Ave, City of Portland and New York Midtown. The journey, including transfers, takes approximately 30h 3m.

How far is it from South Portland to Chicago?

The distance between South Portland and Chicago is 915 miles. The road distance is 1043.4 miles.

How do I travel from South Portland to Chicago without a car?

The best way to get from South Portland to Chicago without a car is to bus and train which takes 26h 14m and costs $240 - $650.

How long does it take to get from South Portland to Chicago?

It takes approximately 5h 34m to get from South Portland to Chicago, including transfers.

Where do I catch the South Portland to Chicago bus from?

South Portland to Chicago bus services, operated by Flixbus USA, depart from City of Portland station.

Bus or fly from South Portland to Chicago?

The best way to get from South Portland to Chicago is to fly which takes 5h 34m and costs $130 - $750. Alternatively, you can bus, which costs $150 - $280 and takes 30h 3m.

Where does the South Portland to Chicago bus arrive?

South Portland to Chicago bus services, operated by Flixbus USA, arrive at New York Midtown station.

What is the time difference between South Portland and Chicago?

Chicago is 1h behind South Portland. It is currently 12:27 PM in South Portland and 11:27 AM in Chicago.

Can I drive from South Portland to Chicago?

Yes, the driving distance between South Portland to Chicago is 1043 miles. It takes approximately 19h 15m to drive from South Portland to Chicago.

Where can I stay near Chicago?

There are 1304+ hotels available in Chicago.

South Portland to Chicago - 7 ways to travel via train, plane, bus, and car

There are 7 ways to get from South Portland to Chicago by plane, bus, train, bus (Flixbus), or car

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2Rio's travel planner.

Fly Portland to Chicago Midway International Airport
best
1. Fly from Portland (PWM) to Chicago Midway International Airport (MDW)plane PWM - MDW
5h 34m
$136–713
Fly Portland to Chicago O'Hare International Airport
cheapest
1. Fly from Portland (PWM) to Chicago O'Hare International Airport (ORD)plane PWM - ORD
6h 14m
$86–443
Bus, train
1. Take the bus from Portland, ME to Boston, MA - South Stationbus Portland / ...
2. Take the train from Boston to Chicago Union Stationtrain Lake Shore Limited
26h 14m
$245–603
Bus (Flixbus)
1. Take the bus from City of Portland to New York Midtownbus FlixBus N2615
2. Take the bus from New York Midtown to Chicago Bus Stationbus FlixBus N2640
30h 3m
$154–278
Drive 1,037.4 mi
1. Drive from South Portland to Chicagocar 1,037.4 mi
19h 15m
$190–274
Bus to Boston Logan Airport, fly to Chicago Midway International Airport
1. Take the bus from Portland, ME to Logan International Airportbus
2. Fly from Boston Logan Airport (BOS) to Chicago Midway International Airport (MDW)plane BOS - MDW
7h 36m
$118–533
Bus to Boston Logan Airport, fly to Chicago O'Hare International Airport
1. Take the bus from Portland, ME to Logan International Airportbus
2. Fly from Boston Logan Airport (BOS) to Chicago O'Hare International Airport (ORD)plane BOS - ORD
7h 57m
$158–423

South Portland to Chicago by bus and train

7Weekly Services

26h 14mAverage Duration

$245Cheapest Price

See schedules

Questions & Answers

Map of how to get from South Portland to Chicago.

Launch map view

Distance: 909.6 mi
Duration: 5h 34m

What companies run services between South Portland, ME, USA and Chicago, IL, USA?

Southwest Airlines flies from Portland (PWM) to Chicago Midway International Airport (MDW) once daily. Alternatively, you can take a bus from Danforth St + High St to Chicago Bus Station via Congress St + Forest Ave, City of Portland, and New York Midtown in around 30h 3m.

Airlines

Train operators

Bus operators

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