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Journey information
Overview: Portland, OR to Chicago, IL flight
USAUSA
Flights from Portland, OR to Chicago, IL depart on average 44 times per day, taking around 4h 10m. Cheap flight tickets for this journey start at $96 (€78) 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 4h 5m. September 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 10m |
Cheapest ticket price $96 (€78) |
Flights per day 44 |
Direct flights 5 |
Fastest flight 4h 5m |
Cheapest month to travel September |
First flight 00:07 |
Last flight 23:58 |
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
The cheapest and fastest flights from Portland, OR to Chicago, IL
Showing times and prices for Dec 01
Cheapest price
$230
Average price
$235
Fastest journey
7 h 25 m
Average duration
10 h 9 m
Flights per day
2
Distance
2823 km
Cheap tickets
The best way to find a cheap flight ticket from Portland, OR to Chicago, IL is to book your journey as far in advance as possible and to avoid traveling at rush hour.
The average ticket from Portland, OR to Chicago, IL will cost around $235 if you buy it on the day, but the cheapest tickets can be found for only $230.
Fast flights
Of the 2 flights that leave Portland, OR for Chicago, IL onMon, Dec 01, 2 travel direct so it’s quite easy to avoid journeys where you’ll have to change along the way.
On Mon, Dec 01 the direct flights cover the 2823 km distance in an average of 10 h 9 m but if you time it right, some flights will get you there in just 7 h 25 m .
On Mon, Dec 01 the longest flights will take 12 h 53 m and usually involve a change or two along the way, but you might be able to save a few pennies if you’re on a budget.
07:07PM7h25
Portland, OR02:32AMChicago, IL
$2301One-way
0 transfers
10:10PM12h53
Portland, OR11:03AMChicago, IL
$2391One-way
0 transfers
07:07PM7h25
Portland, OR02:32AMChicago, IL
$2301One-way
0 transfers
10:10PM12h53
Portland, OR11:03AMChicago, IL
$2391One-way
0 transfers
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 flight with prices starting from €78. For those with little time consider booking a flight which can get you there in 4h 10m. 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 flight costs an average of €78, and a train costs an average of €119.
Distance: 1754 miles (2823 km)
Compare flight with
| Flight | Most popular Train | Bus |
|---|---|---|
€215 Average price Cheapest | €336 Average price | €274 Average price |
7h 10m Average total duration Fastest 4h 10m Onboard + 3h 0m Additional time* | 47h 50m Average total duration 47h 20m Onboard + 30m Additional time* | 72h 20m Average total duration 71h 50m Onboard + 30m Additional time* |
8.5 - 16.9kg CO2 emissions | 0.8 - 2.5kg CO2 emissions Lowest | 2.8 - 7.1kg CO2 emissions |
Direct Options | Direct Options | Direct Options |
Additional time: Average total travel duration to departure point, security checks and transfers.
Live departures
Portland, OR to Chicago, IL flight times
The table below shows live departures for Portland, OR to Chicago, IL flights for today, Sunday, November 30. You can also manually refresh the results below to see updated flight journeys.
Last updated at 6:18 PM
| Provider | Departs | Duration | Arrives | Transfers | Tickets |
|---|---|---|---|---|---|
| 10:10 PM Portland, OR | 12h53 | 11:03 AM Chicago, IL | 0 transfersDirect | |
This is the last flight of the day. | |||||
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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Airlines: Spirit Airlines, American Airlines, Alaska Airlines from Portland, OR to Chicago, ILFind the best flights between Portland, OR to Chicago, IL with Omio's travel partners Spirit Airlines, American Airlines, Alaska Airlines from $96 (€78). 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
4h 7m
Cheapest Price
$122 (€99)
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 3m
Cheapest Price
$194 (€157)
Alaska Airlines frequency
30 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
$96 (€78)
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.
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 $64 (€52) when you book in advance. The average flight ticket price for Portland, OR to Chicago, IL is $155 (€126); however, prices vary depending on the time of day and class and they tend to be more expensive on the day.
On average the Portland, OR to Chicago, IL flight time is 4 h 1 min covering the 1750 mile (2822 km) long journey, but the journey time can vary depending on specific dates or if traveling on weekends and holidays.
The earliest flight from Portland, OR to Chicago, IL leaves at 12: 08AM. Plan your trip with the Journey Planner from Omio.
The latest flight from Portland, OR to Chicago, IL leaves at 11: 58PM.
There are 47 flights a day from Portland, OR to Chicago, IL which require at least one change with United, Alaska Airlines, American Airlines or Spirit Airlines. Schedules can vary on holidays or weekends with fewer flights.
Take the Portland, OR to Chicago, IL flight with United, Alaska Airlines, American Airlines or Spirit Airlines. However, it's always good to check out all possible airlines for the route between Portland, OR and Chicago, IL as there might be differences in the amenities they offer.
The cheapest month to travel from Portland, OR to Chicago, IL by plane is February.
You have options as you can travel from Portland, OR to Chicago, IL 3 different ways: train, bus or flight.
Since neither Portland, OR nor Chicago, IL are in the Schengen Area, passport requirements depend on the specific immigration rules of USA and USA. 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.
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 seasons to visit Chicago, IL are Spring or Summer. The best weather to explore Chicago, IL is during May-September.
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.
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.
popular airports
Popular airports from Portland, OR to Chicago, IL
Portland
Chicago
The major airport for departures in Portland is Portland International Airport. Find all the information you need to know about services, amenities and connections at Portland International Airport for your trip from Portland to Chicago.
Amenities at airport
Wifi
Shopping
Parking
Dining
ATM
Taxis
Accessibility
WC
Hotel
Shower
Lounge
Lost and Found Office
Car Rentalinformation
Distance to city center
8 km
Car connection
I-205, Exit 24AWifi
- Free Wi-Fi available throughout the airport.
Shopping
- Shops in concourses, including Powell's Books and Made in Oregon.
Parking
- Parking available at all terminals, approximately 4.7€ ($5) per hour.
Dining
- Restaurants in concourses, including Burgerville and Mo's Seafood
Taxis
- Available outside the terminal.
Accessibility
- Ramps, assistance
WC
- Available throughout the airport.
Hotel
- Hotels nearby, including Sheraton Portland Airport Hotel.
Shower
- Showers available at the PDX Conference Center, fee applies.
Lounge
- Lounges available, including Alaska Lounge and Delta Sky Club.
Lost and Found Office
- Lost and Found located on the mezzanine level of the terminal.
Car Rental
- Car rental services available on the first floor of the parking garage
Public transit options for Portland International Airport
- MAX Red Line, Portland Intertiol Airport station, 40 minutes
The major airport for arrivals in Chicago is O'Hare International Airport. Find all the information you need to know about services, amenities and connections at O'Hare International Airport for your journey to Chicago from Portland.
Amenities at airport
WifiShoppingParkingDiningATMTaxisAccessibilityWCHotelShowerLoungeLost and Found OfficeCar Rentalinformation
Distance to city center
3 kmCar connection
I-190, Exit 1Wifi
- Free Wi-Fi available throughout the airport.
Shopping
- Shops are located in all terminals, including duty-free and brands like Hudson and MAC Cosmetics.
Parking
- Parking available with options including hourly, daily, and economy lots, approximately 2.85€ ($3) per hour.
Dining
- Restaurants are located in all terminals, offering a variety of cuisines including American and intertiol. Top options include Tortas Frontera and Publican Tavern.
Taxis
- Available outside the terminal.
Accessibility
- Elevators, ramps, toilets
WC
- Available throughout the airport.
Hotel
- Hotels such as Hilton Chicago O'Hare are located on airport grounds, with others like the Hyatt Regency nearby.
Shower
- Showers are available in some lounges, such as the United Club, but access may require a fee or membership.
Lounge
- Lounges available, including United Club and American Airlines Admirals Club.
Lost and Found Office
- Lost and Found located in terminal 1, near the baggage claim area.
Car Rental
- Car rental services are available at the Multi-Modal Facility, with companies like Hertz and Avis.
Public transit options for O'Hare International Airport
- CTA Blue Line, O'Hare Station, 45 minutes to city center
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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