Cheap Flights from Portland (PDX) to Chicago (CHI)

Last minute flights from Portland to Chicago

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Prices shown below were available within the past 3 days for the period specified and should not be considered the final price offered. Please note that availability and prices are subject to change.

Portland Chicago

BEST

DEAL

Wed, 01 Jan PDX - MDW

Mon, 06 Jan MDW - PDX

$303 $292

Prime price per passenger

Portland Chicago

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DEAL

Mon, 06 Jan PDX - ORD

-23 %

$45 $35

Prime price per passenger

Portland Chicago

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DEAL

Thu, 09 Jan PDX - MDW

Sun, 12 Jan MDW - PDX

$139 $134

Prime price per passenger

Portland Chicago

BEST

DEAL

Wed, 25 Dec PDX - ORD

Tue, 31 Dec ORD - PDX

$225 $215

Prime price per passenger

Portland Chicago

BEST

DEAL

Tue, 31 Dec PDX - ORD

Mon, 06 Jan ORD - PDX

$158 $152

Prime price per passenger

Portland Chicago

BEST

DEAL

Tue, 14 Jan PDX - MDW

Fri, 31 Jan MDW - PDX

$143 $137

Prime price per passenger

Route information

Distance: 1750 miles

Portland airports

Portland International Airport (PDX) How far from city center: 6 miles

Chicago airports

O'hare International Airport (ORD) How far from city center: 14 miles

Midway Airport (MDW) How far from city center: 4 miles

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Discover Affordable Airfare from Portland (PDX) to Chicago (CHI)

Flights to Chicago from Portland

Have you been dreaming lately about heading off to your dream destination in United States? Whether you're planning a getaway from Portland or looking for inspiration and ideas to travel to Chicago, eDreams has you covered. We have outstanding flight deals for your trip!

Keep reading to discover everything you need to know before your trip, along with the best tips and tricks to find the best deals and book your flight most easily and conveniently. Our essential information and expert advice will help ensure your travels in United States go as smoothly as possible.

Choosing eDreams means selecting a travel companion that simplifies the art of trip planning. Get your booking today with Europe’s largest travel agency and let us help you prepare for your next adventure at the lowest price.

Finding cheap flights with eDreams

At eDreams, we’re committed to offering the best deals for your flight to Chicago (CHI) from Portland (PDX). To ensure you lock in the lowest prices, just follow these simple steps. Take a look and start saving without sacrificing comfort!

Here are 3 tips for finding low-cost flights:

1. Book your flight to CHI in advance: Try to book your flights several weeks or even months ahead of your travel date. Airlines often offer the lowest fares when tickets first become available.
2. Use our price comparison tool: eDreams’ platform allows you to compare prices across multiple airlines and dates in one place. By searching through our wide range of options, you’ll easily find the best deals for your trip.
3. Be flexible with dates and destinations: If you’re open to adjusting your travel dates or even the destination, you can often find significantly lower prices. Traveling during off-peak times or mid-week can also lead to better savings.

Top airlines flying from Portland to Chicago

You can book regular flights on this route with a bunch of different airlines, offering various service options, from economy to premium, to fit different budgets and preferences. Here are 5 tips to travel comfortably and stay relaxed during a long-haul flight:

1. Wear comfortable clothing: Opt for loose-fitting, breathable clothes and shoes you can easily slip on and off. Layer up so you can adjust to the plane’s temperature.
2. Stay hydrated: Airplane cabins can be dry, so drink plenty of water throughout the flight to stay hydrated. Avoid too much caffeine or alcohol, which can dehydrate you.
3. Move around regularly: Get up and stretch or take a short walk up the aisle every few hours to improve circulation and prevent stiffness.
4. Bring travel essentials: Pack a neck pillow, noise-canceling headphones, an eye mask, and a blanket or shawl for added comfort and to help you sleep more easily.
5. Keep yourself entertained: Download movies, music, podcasts, or eBooks beforehand, and bring a portable charger to keep your devices powered throughout the flight. Staying entertained will make the time pass more quickly.

How long does a flight from Portland to Chicago last

The distance between Portland and Chicago varies depending on if it is a direct, or a non-direct flight. To make your journey more comfortable, we recommend packing essentials like comfortable clothing and travel pillows for added relaxation. Don’t forget to bring entertainment, such as books, magazines, or downloaded movies, to help pass the time.

Main airports in Portland and Chicago

Portland airport’s facilities

At Portland airports, you’ll find various amenities to make the wait more enjoyable. Whether you want to browse luxury shops, enjoy a gourmet meal, or pick up some last-minute souvenirs, there’s plenty to explore. You can also grab a bestseller to read during the flight, or take advantage of the free Wi-Fi to catch up on work or stream entertainment. Make the most of your time at the airport and relax before your journey begins.

Arrival tips for Chicago

Chicago is served by several airports. Once you’ve collected your baggage, it’s a good idea to ensure your phone has an active internet connection before leaving the airport. If you require a local SIM card, airport shops are a convenient option, although they may come at a slightly higher price compared to stores in the city.

In addition to staying connected, take a moment to plan your transportation to your accommodation. Whether you choose a taxi, public transportation, or a pre-booked shuttle, it's best to know your options ahead of time. Airport staff at can assist you with recommendations and details at the information desk, helping you find the easiest and most convenient way to reach your destination.

Booking your flight from Portland to Chicago

Booking your cheap flights with eDreams is straightforward and user-friendly. Start by entering Portland and Chicago as your departure and arrival cities. Then, select your travel dates and initiate the search. Our advanced search engine will sift through thousands of routes and flight combinations to present you with the best deals available.

To make your search even easier, take advantage of our ‘Smart Choice’ feature. This option highlights the most competitive flights at the top of the results, ensuring you find great value quickly. Additionally, you can refine your search by applying filters to view only flights to a specific airport, with your preferred airlines. This customization helps you narrow down your options based on your specific preferences, making it simple to find the perfect flight for your trip.

How to take advantage of flight price updates

Flight fares are determined by a sophisticated pricing algorithm that considers demand and seat availability. Consequently, the price of your flight may change while you’re booking. To lock in the best rate for your trip to Chicago, book your ticket as soon as you find a fare that fits your budget.

Exclusive discounts for Prime member's

As an eDreams Prime member, you'll unlock exclusive deals and save significantly on flights, hotels, and car rentals, plus enjoy a range of additional benefits. Become part of the world’s largest travel membership community and explore all the perks that come with eDreams Prime.

Finding last-minute deals with eDreams

eDreams provides a variety of last-minute flight options at competitive rates. Although these flights can sometimes be pricier, especially during peak travel periods in United States, we offer a selection of choices to meet your needs. To improve your chances of securing a better deal, consider being flexible with your travel dates.

Check in before your flight

Online check-in usually opens 24 to 48 hours before the departure time. Once your booking with eDreams is completed, we’ll email you one week before your day of departure with instructions on how to check in for your flight.

Tips for early check-in with eDreams:

1. Use the eDreams check-in feature: Log in to your eDreams account and navigate to your booking details. Many times, you can check in directly through our platform, streamlining the process and ensuring you don’t miss your check-in window.
2. Receive notifications: Ensure you have notifications enabled for your eDreams account. We’ll send you reminders about your flight, including when check-in is available, so you can complete it as soon as possible.
3. Review your booking details: Double-check your booking details and travel documents in your eDreams account. Ensuring everything is correct can prevent issues during check-in and help you get through the process smoothly.

Best season to travel to Chicago

United States offers a wealth of experiences, from its rich culinary scene and vibrant culture to its breathtaking natural landscapes. The best time to visit depends on your personal preferences and schedule. Consider factors such as the climate, peak tourist periods, and the type of experience you want.

During peak season, expect larger crowds and a bustling atmosphere with abundant cultural and tourist activities. Traveling during the off-season can offer a quieter experience, with fewer tourists, lower prices on flights and accommodations, and a more authentic look at local life. While some outdoor activities might be limited by weather, popular attractions will generally be less crowded, providing a more immersive experience.

The weather in Chicago

The weather in Chicago changes with the seasons. Be sure to pack accordingly to the season you are going to travel. Also, remember to bring an umbrella—it can offer UV protection on sunny days as well!

Best things to do in Chicago

Discover the vibrant charm of Chicago with a wide range of activities for all interests. Whether you're drawn to iconic landmarks, rich historical sites, or diverse cultural experiences, there's something for every traveler to enjoy.

Immerse yourself in the city's heritage by exploring renowned landmarks and museums, and savor the diverse cuisine of United States. If outdoor adventures are more, your style, don’t miss the opportunity to experience the stunning natural landscapes of United States. Whether you're traveling solo, as a couple, or with family, the city offers something special for everyone.

How many days to visit Chicago

To fully experience Chicago, 3 to 7 days should be sufficient. This timeframe allows you to explore major attractions and take in the city’s atmosphere at a comfortable pace. If you have extra time, you can delve into the most authentic neighborhoods, enjoy the local culinary scene, and unwind by strolling through its pedestrian areas.

Car rental to move around Chicago

Renting a car in Chicago is a fantastic way to explore beyond the city limits at your own pace. It allows you to customize your itinerary based on your schedule and budget, especially if you plan to stay in the country for more than a week.

Book your flight from Portland to Chicago

Discover unbeatable flight deals on eDreams. To complete your booking, simply select your travel dates, choose a hotel, and secure a fantastic car rental. Don’t delay—reserve your affordable flight from Portland to Chicago today!

At eDreams, we offer comprehensive information on over 155,000 flight routes, 690 airlines, 2.1 million hotels worldwide, and 40,000 destinations. Our extensive range of vacation packages can help you save significantly on your next journey.

Take advantage of this chance to snag an excellent deal for your upcoming trip—book your flight now!

Frequently asked questions about flights from Portland to Chicago

What are the benefits of booking flexible flight tickets?

Using the flexible flight ticket, you're guaranteed a refund or a rebooking option (without fees) in case of flight cancellations when travelling to United States. At eDreams have you covered!

For flights from Portland to Chicago, how can I find the cheapest price?

The cheapest price for a flight from Portland to Chicago is $35. At eDreams we use different machine learned based methodologies to find our costumers the best option available, considering airline combinations, stopovers and direct flights as well as different criteria for inbound and outbound journeys.

When booking, when is the best time to get the best prices for flights from Portland to Chicago?

The most popular months to book a trip from Portland to Chicago are July, March and April, based on the searches of our customers.

When is the best time to travel from Portland to Chicago?

The best time of the year to visit Chicago depends on lots of personal preferences, especially the price. Regarding popularity, June is the best month to fly to Chicago from Portland in terms of searches from our customers, followed by May and July. If you prefer to avoid the busy season and get away from the crowds January, February and November are the months with fewer searches for Portland - Chicago.

How long does the flight from Portland to Chicago take?

Flight length from Portland to Chicago is around 04:05 hours on average, at an average distance of 2,792 km, for flights for the route (which may have 1 or more stops in other cities in between).

Which airports have flights between Portland and Chicago?

The main route from Portland to Chicago is: Portland International Airport (PDX) to O hare International Airport (ORD). The following airlines fly this route: United Airlines. Alaska Airlines. American Airlines.

The airlines that fly indirectly from Portland to Chicago are:

Spirit Airlines, stopping at Las Vegas during at least 254 minutes.

Flying Time 4 h and 5 m When flying from Portland to Chicago, this can take around 4 h and 5 m in flying time, however this flight duration can vary due to other factors

Cheapest flight $35 The best price for flights from Portland to Chicago offered by eDreams, which have been found by our customers in the last 3 days

Departure Airport Portland International Airport Portland International Airport is where you'll take off when flying from Portland to Chicago

Arrival Airport Midway Airport You'll land at Midway Airport when flying from Portland to Chicago