Portland, OR, USA to Chicago, IL, USA from $90: 5 ways by bus, train, flight or car

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How to Get from Portland to Chicago: Cheapest, Fastest and Best Way

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$90 by trainBest price

2837 kmDistance

6h 1m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Portland to Chicago with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.

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Traveling From Portland to Chicago

The journey from Portland to Chicago reveals a fascinating shift from the laid-back, nature-oriented vibes of the Pacific Northwest to the vibrant, bustling energy of the Windy City.

Best Neighbourhoods in Chicago

Chicago boasts diverse neighborhoods, each with its own distinct charm.

Wicker Park

• Trendy shops and vibrant street art

• Thriving music and nightlife scene

Lincoln Park

• Scenic parks and waterfront views

• Home to Lincoln Park Zoo and museums

Chinatown

• Authentic Asian dining experiences

• Rich cultural festivals and markets

Best Times To Visit Chicago's Attractions

Timing your visits to Chicago's attractions can greatly enhance your experience.

Millennium Park

Visit early morning or weekdays to enjoy serenity and fewer crowds.

The Art Institute of Chicago

Late afternoons on weekdays often offer a more peaceful viewing experience.

Navy Pier

Go during the week or off-season to avoid large tourist groups.

Chicago Weather: What to Expect Year-Round

Chicago experiences a continental climate with cold winters and warm summers, making spring and fall ideal times to visit for pleasant temperatures. Weather greatly influences your travel experiences, as frigid winters can shift plans indoors, while summer brings vibrant street festivals and outdoor activities.

Dining Recommendation in Chicago

Try the iconic Chicago deep-dish pizza at Lou Malnati's, where the rich, buttery crust filled with gooey cheese and chunky tomato sauce creates a hearty experience distinct from Portland's lighter fare. The lively atmosphere and local tradition surrounding this dish provide a culinary adventure that contrasts beautifully with Portland's farm-to-table style.

Portland - Chicago operators

Explore transport companies operating between Portland and Chicago, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.

Plane

Website

southwest.com

Plane from Portland (PDX) to Chicago Midway (MDW)

Average Duration

3h 55m

Estimated price

$210-700

Plane from Portland (PDX) to Chicago Midway (MDW)

Average Duration

6h 21m

Estimated price

$220-700

Plane from Portland (PDX) to Chicago Midway (MDW)

Average Duration

7h 50m

Estimated price

$220-700

Website

delta.com

Plane from Portland (PDX) to Chicago Midway (MDW)

Average Duration

7h 45m

Estimated price

$220-500

Plane from Portland (PDX) to Chicago O'Hare (ORD)

Average Duration

6h 16m

Estimated price

$170-390

Website

united.com

Plane from Portland (PDX) to Chicago O'Hare (ORD)

Average Duration

4h 2m

Estimated price

$160-650

Website

aa.com

Plane from Portland (PDX) to Chicago O'Hare (ORD)

Average Duration

3h 58m

Estimated price

$190-600

Website

alaskaair.com

Plane from Portland (PDX) to Chicago O'Hare (ORD)

Average Duration

4h 6m

Estimated price

$160-490

Train

Contact phone

+1 800-872-7245

Website

amtrak.com

Train from Portland to Chicago Union Station

Average Duration

46h

Estimated price

$90-600

Bus

Contact phone

+1 (855) 626-8585

Website

flixbus.com

Bus from Portland Curbside Bus Stop to Boise

Average Duration

10h 55m

Estimated price

$40-140

Bus from Boise to Provo Intermodal Hub

Average Duration

8h 10m

Estimated price

$30-110

Bus from Provo Central Station to Green River

Average Duration

2h 50m

Estimated price

$30-160

Bus from Green River to St Louis Bus Station

Average Duration

24h 45m

Estimated price

$130-250

Bus from St Louis Bus Station to Chicago Bus Station

Average Duration

6h 39m

Estimated price

$35-85

Contact phone

+1 208-656-8824

Website

saltlakeexpress.com

Bus from Provo Central Station to Green River

Average Duration

2h 50m

Estimated price

$30-160

Contact phone

+1 214-849-8100

Website

greyhound.com

Bus from Green River to St Louis Bus Station

Average Duration

24h 45m

Estimated price

$130-250

Bus from St Louis Bus Station to Chicago Bus Station

Average Duration

6h 39m

Estimated price

$35-85

Portland to Chicago: Overview of Bus, Train, Flight, and Car Trips

Traveling between Portland and Chicago offers a variety of convenient options to suit your preferences, schedule, and budget. Whether you prioritize affordability, speed, or comfort, you’re sure to find the perfect way to travel without compromising on quality or convenience.

🚗 Embark on a scenic road trip from Portland to Chicago, covering a distance of 3432.7 km in approximately 32 hours and 37 minutes of driving time. Enjoy the changing landscapes as you journey from the lush Pacific Northwest to the bustling Midwest city. 💰 The cost of traveling from Portland to Chicago by car ranges between $380 to $600, providing flexibility for different budgets.

Average price

$380 - $600

🚆 Traveling from Portland to Chicago by train is a scenic journey that takes approximately 46 hours. 🌆 For travelers seeking a route with transfers, one option involves stops in Seattle and Milwaukee before reaching Chicago. This route spans 3543.8 km and takes about 2 days, with beautiful scenery along the way. 🛤️ Another route option is a direct journey from Portland to Chicago, covering a distance of 3542.2 km in about 1 day 23 hours.

Departure Point

Portland station

Arrival Point

Chicago Union Station

Useful tips for train travellers

• On your journey from Portland to Chicago, you’ll primarily be traveling with Amtrak. Onboard, Amtrak offers catering services that include a café car where you can purchase snacks, meals, and beverages. Be sure to check their menu online prior to your trip for options, and consider using the Amtrak app to pre-order some meals to enjoy during the ride.

• Amtrak provides various seating options for your trip. These include Coach Class, which is the standard seating with comfortable seats, and Business Class, which offers wider seats and complimentary soft drinks. If you're looking for a more luxurious experience, consider booking First Class on select trains, where you can also enjoy access to exclusive lounges at stations and more expansive options for in-seat service.

• Arriving in Chicago, you'll be at Union Station. It's highly recommended to familiarize yourself with the station layout beforehand. The station offers luggage storage services for a fee if you want to explore the city without your bags. There are clean restrooms available, but showers are not provided. To get from Union Station to the city center quickly, consider taking the Blue Line train; it’s about a 30-minute ride to the downtown area. You can catch the train from the nearby Ogilvie Transportation Center. For more info, visit the Chicago Transit Authority website (transitchicago.com).

🛫 Flying from Portland to Chicago is convenient with a quick direct flight that takes approximately 3 hours and 55 minutes. You can choose between Delta and Southwest Airlines for this route, ensuring a variety of options for your journey. 🌆 Upon arrival in Chicago Midway Airport, you can expect a flight duration of around 6 hours and 1 minute from Portland. This allows for a smooth and efficient travel experience from the West Coast to the Midwest. 💸 Prices for flights between Chicago and Portland can range from $104 to $508, offering flexibility for travelers with different budget considerations.

Departure Point

Portland Airport

Arrival Point

Chicago Midway Airport

🚌 The bus journey from Portland to Chicago involves multiple transfers and takes approximately 2 days and 9 hours. 🛤️ Route 1 by train offers a different option, taking 1 day and 23 hours to cover the 3542.2 km distance with a transfer in Seattle. 💰 Prices for the bus trip between Chicago and Portland range from $267 to $736.

Departure Point

Portland Curbside Bus Stop station

Arrival Point

Chicago Bus Station

Frequently asked questions

Find out more about the route from Portland to Chicago.

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The distance between Portland and Chicago is approximately 2840.5 km, with a road distance of 3432.6 km. Traveling by train, it takes about 46 hours to reach Chicago from Portland, while a plane journey takes around 6 hours and 1 minute. If driving, the trip from Chicago to Portland takes about 32 hours and 37 minutes.

The most cost-effective way to travel from Portland to Chicago is by train, with tickets costing between $90 to $600 and a travel time of 46 hours. However, the most time-efficient option is to fly, with flights taking 6 hours and 1 minute and costing between $100 to $550.

When traveling from Portland to Chicago the prices for a train ticket range from $90 to $600. On the other hand, the prices for a bus ticket for the same route vary between $267 and $736.

To travel from Portland to Chicago without using public transportation, you can drive the distance of approximately 3432.7 km, which takes around 32 hours and 37 minutes. Driving allows for the flexibility to explore various places along the way and the cost can range from $380 to $600 depending on factors such as gas prices and stops made during the journey.

To travel from Portland to Chicago without a car, the best options are to take a train, which typically takes around 46 hours and costs between $90 and $600. Another convenient mode of transportation is by plane, which takes approximately 6 hours and costs between $100 and $550. You can also consider taking a bus, which usually requires about 2 days and 9 hours and costs between $260 and $750.

Yes, there is a direct train link between Portland and Chicago operated by Amtrak, with services departing twice daily and taking approximately 46 hours to reach Chicago Union Station. However, there is no direct bus route from Portland to Chicago, with the journey involving transfers and taking approximately 2 days and 9 hours to complete.

The quickest direct flight from Portland Airport to Chicago Midway Airport typically takes 3 hours and 55 minutes. The cost of a flight between Chicago and Portland ranges from $104 to $508, depending on the airline, time of booking, and other factors.

In Chicago, there is a wide range of accommodation options available, with over 1576 hotels to choose from. Prices for hotels in the city start at $67 per night, offering budget-friendly options for travelers. Visitors can find lodging in various neighborhoods of Chicago, ranging from luxury hotels along the Magnificent Mile to boutique hotels in trendy areas like Wicker Park and Logan Square.