- Must visit
Portland Museum of Art
Leading regional museum with strong American and European art, notable Winslow Homer works, and a handsome historic campus.
Flights from Chicago, IL to Portland, ME depart on average 46 times per day, taking around 4h 12m. Cheap flight tickets for this journey start at $160 but you can travel from only $91 by bus.
There are 3 flights per day. The earliest flight runs at 05:00, the last at 21:40. The fastest flight covers the 889 miles (1432 km) distance in 2h 19m. October is the cheapest month to fly.
Distance 889 miles (1432 km) |
Average flight duration 4h 12m |
Cheapest ticket price $160 |
Flights per day 46 |
Direct flights 3 |
Fastest flight 2h 19m |
First flight 5:00 AM |
Last flight 9:40 PM |
Cheapest Month Oct |
Cheapest Day Wed |
High Season Jul - Sep |
Low Season Jan - Mar |
Omio recommends booking the flight as it is the most popular option from Chicago, IL to Portland, ME among Omio's users. If you are prioritising price, take the bus, with an average ticket price of $177 For those with little time, consider booking a flight, which has an average total journey time of 6h 12m. Average ticket prices depend on the travel mode: a bus costs an average of $177, while a train costs an average of $639.
Distance: 889 miles (1432 km)
Most popular Flight | Bus | Train | Driving |
|---|---|---|---|
$577 Average price | $177 Average price Cheapest | $639 Average price | $215 Average price (fuel + tolls) |
6h 12m Average total duration Fastest 4h 12m Onboard + 2h 0m Additional time* | 29h 24m Average total duration 28h 54m Onboard + 30m Additional time* | 38h 47m Average total duration 38h 17m Onboard + 30m Additional time* | 16h 9m Average total duration (door-to-door) |
![]() Most popular airline | ![]() Most popular bus company | ![]() Most popular train company | Your own car or car rental |
Direct Options | Direct Options | Direct Options | Direct Options |
This is compared to other travel options from Chicago, IL to Portland, ME:
A bus is $399 less than a flight for this route with tickets for a flight from Chicago, IL to Portland, ME costing on average $577.
A bus is $461 less than a train for this route with tickets for a train from Chicago, IL to Portland, ME costing on average $639.
Other travel options to Portland, ME take longer:
Bus takes on average 28h 54m.
Train takes on average 38h 17m.
Compare train, bus, and flight prices over the next three weeks. See the best deals at a glance, find the lowest fares, and choose the option that fits your budget.
Discover the best of Portland, ME — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Portland, ME trip today.
Leading regional museum with strong American and European art, notable Winslow Homer works, and a handsome historic campus.
Hands-on history museum inside Portland Head Light exploring lighthouse technology, shipwrecks, and Maine's maritime past.
Historic home and museum focused on Henry Wadsworth Longfellow, with original furnishings and insight into early Portland life.
Historic district of brick streets, shops, and harbor views; Portland's classic place to stroll, browse, and absorb local character.
Eastern Promenade offers broad Casco Bay views, walking paths, lawns, and one of Portland's best spots for relaxing outdoors.
Hilltop neighborhood with historic homes, local feel, and rewarding lookout points around the Portland Observatory area.
Sweet, cold-water Maine lobster served steamed, in rolls, or with drawn butter. It is the city’s signature catch and a cornerstone of working waterfront food culture.
A creamy New England-style chowder made with local clams, potatoes, and salt pork. It is a classic Maine coastal comfort dish found across Portland.
Freshly shucked oysters from Maine farms such as the Damariscotta River. They are prized for their cold-water brininess and strong connection to local aquaculture.
Refined destination restaurant serving seasonal Maine tasting menus with local seafood and produce. Elegant but warm, and one of Portland’s top fine dining rooms.
Historic market-style venue known for potato donuts, sandwiches, coffee, and local pantry goods. Casual, busy, and deeply rooted in Portland food culture.
Beloved casual seafood shack known for excellent lobster rolls, fried seafood, and harbor views. A classic Portland stop with a relaxed waterfront feel.
Moderate for a U.S. coastal city: hotels peak in summer, seafood dining is mid-priced to high, and local transit is limited so visitors may rely on walking, rideshares, or cars.
Tip 18-20% at restaurants, 15-20% for taxis, and $1-2 per drink or coffee at cafes and bars.
Find answers to the most common questions about traveling from Chicago, IL to Portland, ME by flight. From journey times and ticket prices to direct connections, first and last departures, and even whether the route is scenic, our FAQs cover everything you need to plan your trip. Whether you’re looking for the fastest flight, the cheapest option, or tips for making the most of your visit at Portland, ME, this guide helps you travel smarter and with confidence.

Most Chicago, IL to Portland, ME flights use the O'Hare International Airport to Portland International Jetport airport pair. Use this guide to compare Chicago, IL and Portland, ME airports on this route, check city-centre transport, alongside checking practicalities like airport facilities and services.
O'Hare International Airport is 3 km from Chicago city centre. Public transport options include:
O'Hare International Airport has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Hotel, Shower, Lounge, Lost and Found Office, and Car Rental.
Food options include: Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
Free Wi-Fi available throughout the airport. ATMs are located throughout all terminals.
Lost and found is available at the station.
Available at O'Hare International Airport: Parking, Taxis, WC.
Available at O'Hare International Airport: Car Rental.
Accessibility facilities are available at O'Hare International Airport: Elevators, ramps, toilets.
Nearby hotels include Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby..
Portland International Jetport is 1 km from Portland city centre. Public transport options include:
Portland International Jetport has practical services for this route, including Wifi, Shopping, Parking, Dining, ATM, Taxis, Accessibility, WC, Lounge, Lost and Found Office, and Car Rental.
Food options include: Restaurants available include Linda Bean's Lobster Cafe and Starbucks in the terminal.
Free Wi-Fi available throughout the airport. ATMs are located near the baggage claim area.
Lost and found is available at the station.
Available at Portland International Jetport: Parking, Taxis, WC.
Available at Portland International Jetport: Car Rental.
Accessibility facilities are available at Portland International Jetport: Elevators, ramps.
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