- Must visit
Art Institute of Chicago
World-class art museum with masterpieces from Monet to Hopper and the famous Modern Wing.
No flights found
We are not able to find a flight between these two places.
The cheapest and fastest flightsfrom Portland, OR to Chicago, ILShowing times and prices for Jul 14
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Portland, OR PDX to Chicago, IL CHI flight with American Airlines
Journey information
Overview: Portland, OR to Chicago, IL flight
USAUSA
Flights from Portland, OR to Chicago, IL depart on average 46 times per day, taking around 4h 17m. Cheap flight tickets for this journey start at $59 (€48) if you book in advance.
There are 5 flights per day. The earliest flight runs at 00:07, the last at 23:58. The fastest flight covers the 1754 miles (2823 km) distance in 3h 54m. November is the cheapest month to fly.
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Distance 1754 miles (2823 km) |
Average flight duration 4h 17m |
Cheapest ticket price $59 (€48) |
Flights per day 46 |
Direct flights 5 |
Fastest flight 3h 54m |
First flight 12:07 AM |
Last flight 11:58 PM |
Cheapest Month Nov |
Cheapest Day Sun |
High Season Jan - Mar |
Low Season Apr - Jun |
Busiest Day Sun |
Least Busy Day Sun |
Best time to book 28 days |
Fares are the lowest economy prices found on Omio. Early booking often means lower prices. Prices change daily and are subject to availability. Discount cards, coach trips, and booking fees are not included.
Price information
Travel Information
Compare train, bus, and flight for Portland, OR to Chicago, IL
Omio recommends booking the train as it is the most popular option from Portland, OR to Chicago, IL among Omio's users. If you are prioritising price take the bus with prices starting from $134. For those with little time consider booking a flight which can get you there in 4h 17m. In case you are seeking to minimise your carbon footprint the train is your best bet as it emits only 0.8 - 2.5kg. The ticket price range depends on the travel mode: a bus costs an average of $134, and a train costs an average of $171.
Distance: 1754 miles (2823 km)
Compare flight with
| Flight | Most popular Train | Bus | Driving |
|---|---|---|---|
$359 Average price | $396 Average price | $315 Average price Cheapest | $427 Average price (fuel + tolls) |
7h 17m Average total duration Fastest 4h 17m Onboard + 3h 0m Additional time* | 48h 5m Average total duration 47h 35m Onboard + 30m Additional time* | 73h 20m Average total duration 72h 50m Onboard + 30m Additional time* | 30h 52m Average total duration (door-to-door) |
8.5 - 16.9kg CO2 emissions | 0.8 - 2.5kg CO2 emissions Lowest | 2.8 - 7.1kg CO2 emissions | - CO2 emissions |
 Most popular airline |  Most popular train company |  Most popular bus company | Your own car or car rental |
Direct Options | Direct Options | Direct Options | Direct Options |
Additional time: Average total travel duration to departure point, security checks and transfers.
The cheapest way to travel from Portland, OR to Chicago, IL is a bus with an average price of $315 (€260).
This is compared to other travel options from Portland, OR to Chicago, IL:
A bus is $44 (€36) less than a flight for this route with tickets for a flight from Portland, OR to Chicago, IL costing on average $359 (€296).
A bus is $81 (€67) less than a train for this route with tickets for a train from Portland, OR to Chicago, IL costing on average $396 (€326).
The fastest way to travel from Portland, OR to Chicago, IL is by flight with an average journey time of 4h 17m.
Other travel options to Chicago, IL take longer:
Train takes on average 47h 35m.
Bus takes on average 72h 50m.
It's helpful to compare your options as there are 3 ways to travel between Portland, OR and Chicago, IL including taking a train, bus, and flight.
We recommend using the train as it is the most popular way to get from Portland, OR to Chicago, IL among Omio's users.
Live departures
Portland, OR to Chicago, IL flight times
The table below shows live departures for Portland, OR to Chicago, IL flights for today, Tuesday, July 14. You can also manually refresh the results below to see updated flight journeys.
Last updated at
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| 7:48 PM Portland, OR | 4h09 | 11:57 PM Chicago, IL | 0 transfersDirect | |
 | 8:39 PM Portland, OR | 7h59 | 4:38 AM Chicago, IL | 0 transfersDirect | |
| 9:38 PM Portland, OR | 4h02 | 1:40 AM Chicago, IL | 0 transfersDirect | |
| Wednesday, July 15 | |||||
| 6:59 AM Portland, OR | 3h57 | 10:56 AM Chicago, IL | 0 transfersDirect | |
| 7:35 AM Portland, OR | 3h57 | 11:32 AM Chicago, IL | 0 transfersDirect | |
Find all the dates and times for this journey
Compare prices and tickets Portland, OR to Chicago, IL by train, bus, or flight
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.
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Why should you book Portland, OR to Chicago, IL flights with Omio?
American Airlines as well as Spirit Airlines or Alaska Airlines offer flights services from Portland, OR to Chicago, IL.
Omio is an official ticket reseller for all your travel options from Portland, OR to Chicago, IL.
Why book with Omio vs American Airlines?
- Compare with other providers: On Omio, you can not only buy tickets for American Airlines, but also compare tickets for the likes of Spirit Airlines or Alaska Airlines to find the best option for your trip from Portland, OR to Chicago, IL.
- Designed for International Travelers: Omio is in your language including 24/7 customer service and offers multiple payment options, including PayPal, credit cards, and bank transfer, in your preferred currency.
- Compare all your options: Omio allows you to compare American Airlines with all available travel options, which are train, bus and flight to ensure you get the best deal for traveling from Portland, OR to Chicago, IL.
Why book with Omio over Trip, Edreams or Skyscanner?
- Compare with other providers: On Omio, you can also compare tickets for the likes of Spirit Airlines or Alaska Airlines to find the best option for your trip from Portland, OR to Chicago, IL.
- Multiple modes of transport: Omio allows you to compare travel options including train, bus and flight to find the ideal travel option from Portland, OR to Chicago, IL.
Airlines: American Airlines, Spirit Airlines, Alaska Airlines from Portland, OR to Chicago, ILFind the best flights between Portland, OR to Chicago, IL with Omio's travel partners American Airlines, Spirit Airlines, Alaska Airlines from $59 (€48). We can find you the best deals, schedules and tickets when comparing and booking the best trip.
American Airlines
About
American Airlines is one of the largest airlines in the world, connecting travelers to hundreds of destinations across the United States, Latin America, Europe, Asia, and beyond. Operating from major hubs such as Dallas/Fort Worth, Miami, and Charlotte, American offers a wide range of travel options. Passengers can choose from Economy with affordable fares, Premium Economy with extra space, or Business and First Class featuring flat-bed seats, premium dining, and lounge access. With a modern fleet and membership in the oneworld alliance, American Airlines combines global reach with comfort and reliability.
Luggage & cancellation policy
Average Duration
3h 57m
Cheapest Price
$59 (€48)
American Airlines frequency
4 a day
Luggage included
1 carry-on bag (22 x 14 x 9 inches) and 1 personal item (18 x 14 x 8 inches) included in most fares
Additional luggage
Checked bags fees vary by route. First checked bag typically $30, second $40 on domestic flights
Cancellation Policy
Basic Economy tickets cannot be changed or refunded. Other fares allow changes with fee, refunds subject to fare rules.
Pregnant on board
Passengers can fly up to 36 weeks for single pregnancies, 32 weeks for multiple pregnancies. Medical certificate required within 7 days of departure if within 4 weeks of due date.
Unaccompagned minor
Children ages 5-14 can travel alone using American Airlines Unaccompanied Minor Service. Service fee is $150 each way.
Amenities on board the airplane
Wifi
Food sold onboard
USB plugs
Accessibility
American Airlines provides wheelchair assistance and special services for passengers with disabilities. Assistance must be requested at least 48 hours before departure.
Pets
Small dogs and cats allowed in cabin for $125 fee. Must be in approved carrier under seat. Service animals allowed.
Entertaiment on board
Alaska Airlines
About
Alaska Airlines, headquartered in SeaTac, Washington, is a major U.S. airline and the fifth-largest in North America by scheduled passengers carried as of 2024. Along with its regional partners, Horizon Air and SkyWest Airlines, Alaska Airlines operates a route network primarily connecting cities along the West Coast of the United States, including Alaska and Hawaii, to over 100 destinations in the contiguous U.S., the Bahamas, Belize, Canada, Costa Rica, Guatemala, and Mexico. The airline is a member of the Oneworld alliance, offering passengers access to a broad global network. Alaska Airlines is known for its customer service and loyalty program, Mileage Plan, and offers First Class, Premium Class, and Main Cabin seating options. The airline's primary hub is Seattle-Tacoma International Airport. In 2024, its parent company, Alaska Air Group, acquired Hawaiian Airlines.
Luggage & cancellation policy
Average Duration
4h 10m
Cheapest Price
$370 (€305)
Alaska Airlines frequency
29 a day
Luggage included
1 carry-on bag (22 x 14 x 9) and 1 personal item included
Additional luggage
Checked bags fees start at $30 for first bag, $40 for second bag
Cancellation Policy
Saver fares are non-refundable. Main and First Class fares are refundable with fee, depending on fare type and elite status
Pregnant on board
Passengers can fly up to 36 weeks pregnant. After 28 weeks, medical certificate required
Unaccompagned minor
Unaccompanied minor service available for children ages 5-17. Service fee is $50 per direction on nonstop flights
Amenities on board the airplane
Wifi
USB plugs
Accessibility
Alaska Airlines provides wheelchair assistance and special services for passengers with disabilities, including meet-and-assist services and accessible seating
Pets
Pets allowed in cabin and cargo hold. Service animals welcome. Fees apply for pets in cabin ($100)
Entertaiment on board
Spirit Airlines
About
Spirit Airlines is an American ultra-low-cost carrier, headquartered in Dania Beach, Florida, operating scheduled flights throughout the United States, the Caribbean, and Latin America. Known for its distinctive bright yellow planes, Spirit's business model traditionally focuses on offering low base fares by unbundling services, allowing passengers to pay only for the amenities they choose, such as baggage and seat selection. As of August 2024, Spirit is evolving its offerings, introducing new fare tiers like "Go Big," "Go Comfy," "Go Savvy," and "Go," which include various bundled perks such as wider seats, extra legroom, priority boarding, and in-flight refreshments. Spirit was the seventh largest passenger carrier in North America as of 2023.
Luggage & cancellation policy
Average Duration
7h 17m
Cheapest Price
$94 (€78)
Spirit Airlines frequency
2 a day
Luggage included
Personal item (18 x 14 x 8 inches) included
Additional luggage
Checked bags: First bag $79-89, Second bag $89-99, Additional bags $105-110
Cancellation Policy
Cancellation within 24 hours of booking is free, after that fees apply based on fare type and timing
Pregnant on board
Up to 7 days before departure with medical certificate. After 28 weeks, medical certificate required
Unaccompagned minor
Ages 5-14 can travel as unaccompanied minors for $100 fee per direction. Service not available on international flights or connecting flights
Amenities on board the airplane
Wifi
Accessibility
Spirit Airlines offers assistance for passengers with disabilities, including wheelchair services and priority boarding. Passengers are encouraged to request assistance at least 48 hours in advance to ensure availability.
Complete guide to Chicago, IL
Things to do in Chicago, IL
Discover the best of Chicago, IL — top attractions, local food, transport tips, budget advice, and currency essentials. Plan your perfect Chicago, IL trip today.
- Must visit
Field Museum
Major natural history museum with Sue the T. rex, ancient cultures, and strong family appeal.
- Must visit
Museum of Science and Industry
Hands-on science museum in a grand former fair building, popular for exhibits and a U-505 submarine.
- Must visit
Millennium Park
Lively lakefront park with Cloud Gate, Crown Fountain, gardens, and major public art in central Chicago.
- Must visit
Magnificent Mile
Famous shopping boulevard lined with architecture, hotels, riverfront views, and major city energy.
- Must visit
Chicago Riverwalk
Scenic pedestrian-friendly riverwalk with boat docks, public art, bridges, and standout skyline perspectives.
Deep-Dish Pizza
Deep-dish pizza is Chicago’s iconic pie with a tall buttery crust, layers of cheese and toppings, and chunky tomato sauce baked on top.
Chicago-Style Hot Dog
The Chicago-style hot dog is an all-beef frank on a poppy seed bun with mustard, relish, onion, tomato, pickle, peppers, and celery salt.
Italian Beef Sandwich
Italian beef is thin-sliced roast beef piled onto a roll, often dipped in savory juices and topped with sweet peppers or spicy giardiniera.
Johnnie's Beef
Classic spot for juicy Italian beef sandwiches, especially dipped and topped with spicy giardiniera, with a casual local feel.
Superdawg Drive-In
Legendary stand for Chicago-style hot dogs and char-grilled sausages, served fast in a no-frills local landmark.
Alinea
World-famous fine dining destination offering a highly creative tasting menu and refined service in an elegant setting.
US dollar ($)
Moderate for a major US city: hotels can be pricey, but transit is affordable and dining ranges from cheap eats to upscale options.
Average meal costs
- Budget
- $10-18 for fast food or casual takeout.
- Mid-range
- $20-40 per person for a restaurant meal.
- Fine dining
- $75+ per person for upscale restaurants.
- Coffee
- $3-6 for coffee or cappuccino.
Tipping culture
Tip 18-20% at restaurants, $1-2 per drink at bars, 10-15% for taxis, and optional small change at cafes.
FAQs: Portland, OR to Chicago, IL Flight
Find answers to the most common questions about traveling from Portland, OR to Chicago, IL 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 Chicago, IL, this guide helps you travel smarter and with confidence.
Cheap plane tickets from Portland, OR to Chicago, IL can start from as little as $59 (€48) when you book in advance. The average flight ticket price for Portland, OR to Chicago, IL is $359 (€296) ; however, prices vary depending on the time of day and class and they tend to be more expensive on the day.
The average journey time by plane from Portland, OR to Chicago, IL is 3h 54m to travel the 1754 miles (2823 km) long route. Journey times can vary on weekends and holidays, so use our Journey Planner to search for a specific date.
The earliest flight from Portland, OR to Chicago, IL leaves at 12:07 AM. Plan your trip with the Journey Planner from Omio.
The latest flight from Portland, OR to Chicago, IL leaves at 11:58 PM.
Yes, there are 5 direct flights a day from Portland, OR to Chicago, IL with American Airlines, Alaska Airlines. Schedules can vary on holidays or weekends with fewer direct flights.
When taking a flight from Portland, OR to Chicago, IL, you can count on American Airlines, Spirit Airlines, Alaska Airlines for the best way to get you to Chicago, IL. You can also check all possible airlines who offer a service between Portland, OR and Chicago, IL and compare the amenities they offer before buying a plane ticket.
Flights from Portland, OR to Chicago, IL generally leave from Portland International Airport and arrive in O'Hare International Airport.Portland International Airport is 4 miles (8 km) away from Portland, OR city centre and O'Hare International Airport is 1 miles (3 km) from Chicago, IL city centre.
The cheapest month for a flight from Portland, OR to Chicago, IL is November.
It's helpful to compare your options as there are 3 ways to travel between Portland, OR and Chicago, IL including taking a train, bus, and flight.
Since neither Portland, OR nor Chicago, IL are in the Schengen Area, passport requirements depend on the specific immigration rules of United States and United States. Entry and visa requirements can be subject to change. For the latest information, check with your destination's embassy or consulate.
There is a time difference of 2 h between Portland, OR and Chicago, IL all year round.
The best events to attend in Chicago, IL include:
- Chicago Air and Water Show, an exhilarating display of military and civilian aircraft performing daring maneuvers over Lake Michigan
- Lollapalooza, a massive music festival featuring top artists across multiple genres in Grant Park
- Chicago Gourmet, a premier culinary event celebrating the city's vibrant food scene with tastings, cooking demonstrations, and wine pairings.
Some of the most interesting sights to explore in Chicago, IL are:
- Millennium Park, a public park known for its modern art installations and the iconic Cloud Gate sculpture
- Art Institute of Chicago, a renowned museum housing an extensive collection of art from around the world
- Navy Pier, a popular entertainment destination featuring rides, restaurants, and lakefront views
- Willis Tower Skydeck, an observation deck offering panoramic views of the city from one of the tallest buildings in the Western Hemisphere
- Field Museum, a natural history museum with vast exhibits including the famous T. rex skeleton, Sue.
The best holidays to experience in Chicago, IL include:
- Memorial Day, the unofficial start of summer with vibrant outdoor activities and events
- Independence Day, spectacular fireworks and festive celebrations throughout the city
- Labor Day, a lively atmosphere with various festivals and pleasant weather.
The best things to do in Chicago, IL include:
- Museum of Science and Industry, an interactive museum featuring exhibits on science, technology, and industry
- Explore the vibrant neighborhoods of Chicago, such as Wicker Park and Lincoln Park, known for their unique shops and eateries
- Take a river cruise to see the city's iconic architecture from a different perspective
- Attend a live performance at the historic Chicago Theatre
- Enjoy a day at Lincoln Park Zoo, one of the oldest zoos in the U.S., offering free admission.
The best season to visit Chicago, IL is Spring or Summer. The best weather to explore Chicago, IL is during May-September.
We recommend using the train as it is the most popular way to get from Portland, OR to Chicago, IL among Omio's users.
For domestic flights we recommend to arrive 1.5 to 2 hours before departure. Please check the website of your departure airport if in doubt. Some airports may offer booking time slots for security checks or offer additional information on when to get there based on time of day.
Most airlines permit carry-on bags that fit within specific dimensions (e.g., 22 x 14 x 9 inches or 56 x 36 x 23 cm), including handles and wheels. Bags must fit in the overhead bin or under the seat in front of you.
Many airlines impose weight limits, commonly ranging between 7 kg (15 lbs) and 12 kg (26 lbs). Typically, passengers are allowed one carry-on bag and one personal item (for example a purse, laptop bag, or backpack). Personal items must fit under the seat in front of you. Budget Airlines (like Ryanair or Wizz Air) have stricter size and weight limits, often requiring fees for larger carry-ons. Full-Service Airlines have more lenient policies, sometimes including more spacious dimensions or higher weight limits depending on your ticket class.
The list of items prohibited on an airplane varies by country and airline, but in general, the following items are not allowed in carry-on or checked baggage: Weapons and self-defence items, sharp objects, flammable materials, explosives, toxic substances, or liquids over 100ml (except for medications and baby essentials). In checked baggage, firearms (without authorization), explosives, large lithium batteries, and hazardous chemicals are prohibited. Electronic cigarettes must be in carry-on bags, while alcohol and dry ice have restrictions. Always check with your airline for specific regulations.
The currency used in the United States is the US Dollar (USD). For travelers, using cards is generally more convenient and widely accepted, especially credit and debit cards, while cash is useful for small purchases or places that do not accept cards.
In Chicago, IL, travelers should be cautious of pickpocketing and purse snatching, especially in crowded areas like public transit and popular tourist spots. Common scams include fake charity solicitations and distraction thefts. It is advisable to stay alert in neighborhoods outside downtown after dark and use authorized transportation services to avoid unlicensed taxi scams. Keeping valuables secure and being aware of surroundings helps mitigate these risks.
Pack lightweight, versatile clothing suitable for the destination's climate, and use secure, lockable luggage to protect belongings. Keep essential items like travel documents, medication, and valuables in a carry-on bag for easy access. Use packing organizers or cubes to maximize space and maintain order. Lastly, include a small first aid kit and personal hygiene items for added comfort during travel.
popular airports
Popular airports from Portland, OR to Chicago, IL
Most Portland, OR to Chicago, IL flights use the Portland International Airport to O'Hare International Airport airport pair. Use this guide to compare Portland, OR and Chicago, IL airports on this route, check city-centre transport, alongside checking practicalities like airport facilities and services.
Departure airports in Portland
Arrival airports in Chicago
Which Portland, OR airport do flights to Chicago, IL leave from?
Flights from Portland, OR to Chicago, IL depart from Portland International Airport. The airport is 4 miles (8 km) from Portland, OR city centre at 7000 NE Airport Way, Portland, OR 97218, USA.
Portland International Airport (PDX)7000 NE Airport Way, Portland, OR 97218, USA
City-centre transport
Getting to Portland International Airport from Portland city centre
Portland International Airport is 8 km from Portland city centre. Public transport options include:
BusCentral Oregon Breeze · 30m · $55
12, 292 · 53m · $7 · every ~8 min
292 · 53m · $4
TramMAX Red Line · 30m · $4 · every ~8 min
MAX Red Line · 34m · $4 · every ~8 min
MAX Red Line · 36m · $4 · every ~8 min
Portland International Airport airport facilities and services
Portland 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 and drink
Food options include: Restaurants in concourses, including Burgerville and Mo's Seafood
Wi-Fi and ATMs
Free Wi-Fi available throughout the airport. ATMs are located throughout the airport.
Luggage and lost property
Lost and found is available at the station.
Parking, taxis and toilets
Available at Portland International Airport: Parking, Taxis, WC.
Bike and car services
Available at Portland International Airport: Car Rental.
Accessibility
Accessibility facilities are available at Portland International Airport: Ramps, assistance.
Shops, hotels and contact
Nearby hotels include Hotels nearby, including Sheraton Portland Airport Hotel..
Which Chicago, IL airport do flights from Portland, OR arrive at?
Flights from Portland, OR to Chicago, IL most often arrive at O'Hare International Airport. Some flights land at Saint Paul International Airport, so check your ticket before travel to confirm your Chicago, IL arrival airport.
O'Hare International Airport (ORD)10000 W O'Hare Ave, Chicago, IL 60666, USA
City-centre transport
Getting to O'Hare International Airport from Chicago city centre
O'Hare International Airport is 3 km from Chicago city centre. Public transport options include:
SubwayBlue Line · 1h 7m · $6 · every ~23 min
O'Hare International Airport airport facilities and services
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 and drink
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.
Wi-Fi and ATMs
Free Wi-Fi available throughout the airport. ATMs are located throughout all terminals.
Luggage and lost property
Lost and found is available at the station.
Parking, taxis and toilets
Available at O'Hare International Airport: Parking, Taxis, WC.
Bike and car services
Available at O'Hare International Airport: Car Rental.
Accessibility
Accessibility facilities are available at O'Hare International Airport: Elevators, ramps, toilets.
Shops, hotels and contact
Nearby hotels include Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby..
Most popular flights from Portland, OR
More options for your journey from Portland, OR to Chicago, IL
Here are some other resources that might have the information you need
Most popular flights to and from Chicago, IL and Portland, OR
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