• Our partners include:

  • Greyhound USA
  • VIA Rail
  • Amtrak
  • Acela Express
  • Megabus
  • SuperShuttle
  • Booking.com
  • Skyscanner
  • Airbnb
  • Expedia

There are 6 ways to get from Chicago to Bend by plane, bus, train or car

Select an option below to see step-by-step directions and to compare ticket prices and travel times in Rome2rio's travel planner.

Recommended option

Fly Chicago O'Hare to Redmond  •  7h 44m

  1. Fly from Chicago O'Hare (ORD) to Redmond (RDM) ORD - RDM

$234 - $972

Cheapest option

Fly Chicago Midway to Portland, bus  •  11h 25m

  1. Fly from Chicago Midway (MDW) to Portland (PDX) MDW - PDX
  2. Take the bus from Portland International Airport to Redmond Hub

$213 - $624

4 alternative options

Fly Chicago Midway to Redmond  •  9h 25m

  1. Fly from Chicago Midway (MDW) to Redmond (RDM) MDW - RDM

$264 - $1,121

Fly Chicago O'Hare to Eugene, bus  •  10h 11m

  1. Fly from Chicago O'Hare (ORD) to Eugene (EUG) ORD - EUG
  2. Take the bus from Eugene Greyhound Station to Hawthorne Station Bend

$232 - $510

Train, bus  •  2 days 4h

  1. Take the train from Chicago Union Station to Portland Union Station Empire Builder
  2. Take the bus from Portland Union Station to Redmond Hub Central Oregon Breeze

$244 - $356

Drive  •  31h 47m

  1. Drive from Chicago to Bend 2018.3 miles

$190 - $290

Questions & Answers

The cheapest way to get from Chicago to Bend is to drive which costs $190 - $290 and takes 31h 47m.

More details

The quickest way to get from Chicago to Bend is to fly which costs $230 - $1,000 and takes 7h 44m.

More details

The distance between Chicago and Bend is 1708 miles. The road distance is 2018.3 miles.

Get driving directions

The best way to get from Chicago to Bend without a car is to train and bus which takes 2 days 4h and costs $240 - $360.

More details

It takes approximately 7h 44m to get from Chicago to Bend, including transfers.

More details

The quickest flight from Chicago O'Hare Airport to Redmond Airport is the direct flight which takes 4h 36m.

Search flights

Bend is 2h behind Chicago. It is currently 11:24 AM in Chicago and 9:24 AM in Bend.

Yes, the driving distance between Chicago to Bend is 2018 miles. It takes approximately 31h 47m to drive from Chicago to Bend.

Get driving directions

American Airlines, Delta, Alaska Airlines, Inc. and United Airlines offer flights from Chicago O'Hare Airport to Redmond Airport.

Search flights

There are 1348+ hotels available in Bend. Prices start at $124 USD per night.

More details

Map of how to get from Chicago to Bend.
Launch map view
  • Distance: 1707.9 miles
  • Duration: 7h 44m

What companies run services between Chicago, IL, USA and Bend, OR, USA?

United Airlines, Delta and two other airlines fly from Chicago to Bend hourly.

Airlines
Delta
Website
delta.com
Flights from Chicago O'Hare to Redmond via Salt Lake City
Ave. Duration
7h
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$210 - $900
Flights from Chicago O'Hare to Redmond via Seattle
Ave. Duration
6h 39m
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$220 - $950
Flights from Chicago Midway to Redmond via Minneapolis, Seattle
Ave. Duration
9h 30m
When
Every day
Estimated price
$260 - $1,100
Flights from Chicago Midway to Redmond via Detroit, Seattle
Ave. Duration
11h 4m
When
Every day
Estimated price
$290 - $1,200
Flights from Chicago Midway to Redmond via Detroit, Salt Lake City
Ave. Duration
11h 55m
When
Every day
Estimated price
$280 - $1,200
Flights from Chicago Midway to Redmond via Salt Lake City
Ave. Duration
6h 33m
When
Saturday
Estimated price
$300 - $1,100
Flights from Chicago Midway to Redmond via Seattle
Ave. Duration
7h 1m
When
Monday to Saturday
Estimated price
$320 - $1,200
Flights from Chicago Midway to Redmond via Minneapolis, Salt Lake City
Ave. Duration
12h 48m
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$250 - $1,100
Flights from Chicago O'Hare to Eugene via Salt Lake City
Ave. Duration
6h 26m
When
Every day
Estimated price
$230 - $550
Flights from Chicago O'Hare to Eugene via Seattle
Ave. Duration
7h 20m
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$230 - $550
Flights from Chicago Midway to Portland via Minneapolis
Ave. Duration
6h 13m
When
Monday, Tuesday, Wednesday, Thursday, Friday and Sunday
Estimated price
$240 - $850
United Airlines
Website
united.com
Flights from Chicago O'Hare to Redmond
Ave. Duration
4h 36m
When
Every day
Estimated price
$220 - $950
Flights from Chicago O'Hare to Redmond via Denver
Ave. Duration
6h 52m
When
Every day
Estimated price
$220 - $950
Flights from Chicago O'Hare to Redmond via San Francisco
Ave. Duration
7h 43m
When
Every day
Estimated price
$250 - $1,100
Flights from Chicago Midway to Redmond via Denver
Ave. Duration
6h 57m
When
Sunday
Estimated price
$270 - $1,200
Flights from Chicago O'Hare to Eugene
Ave. Duration
4h 45m
When
Every day
Estimated price
$210 - $650
Flights from Chicago O'Hare to Eugene via Denver
Ave. Duration
6h 56m
When
Every day
Estimated price
$210 - $650
Flights from Chicago O'Hare to Eugene via San Francisco
Ave. Duration
7h 48m
When
Every day
Estimated price
$210 - $650
Flights from Chicago O'Hare to Eugene via Los Angeles
Ave. Duration
7h 49m
When
Every day
Estimated price
$210 - $650
Southwest Airlines
Website
southwest.com
Flights from Chicago Midway to Portland
Ave. Duration
4h 19m
When
Every day
Estimated price
$280 - $900
Flights from Chicago Midway to Portland via Kansas City
Ave. Duration
5h 58m
When
Every day
Estimated price
$280 - $900
Flights from Chicago Midway to Portland via Denver
Ave. Duration
6h
When
Sunday
Estimated price
$280 - $900
Flights from Chicago Midway to Portland via St. Louis
Ave. Duration
6h 10m
When
Saturday
Estimated price
$280 - $900
Alaska Airlines, Inc.
Website
alaskaair.com
Flights from Chicago O'Hare to Redmond via Portland
Ave. Duration
7h 15m
When
Every day
Estimated price
$220 - $950
Flights from Chicago O'Hare to Redmond via Seattle
Ave. Duration
6h 52m
When
Every day
Estimated price
$230 - $950
Flights from Chicago Midway to Redmond via Seattle
Ave. Duration
7h 10m
When
Monday to Saturday
Estimated price
$320 - $1,200
Flights from Chicago O'Hare to Eugene via Seattle
Ave. Duration
6h 52m
When
Every day
Estimated price
$150 - $470
American Airlines
Website
aa.com
Flights from Chicago O'Hare to Redmond via Phoenix
Ave. Duration
7h 25m
When
Every day
Estimated price
$260 - $950
Flights from Chicago O'Hare to Redmond via Los Angeles
Ave. Duration
7h 37m
When
Every day
Estimated price
$270 - $950
Flights from Chicago Midway to Redmond via Phoenix
Ave. Duration
7h 20m
When
Sunday
Estimated price
$350 - $1,200
Flights from Chicago Midway to Redmond via Los Angeles
Ave. Duration
7h 20m
When
Monday to Friday
Estimated price
$360 - $1,300
Flights from Chicago O'Hare to Eugene via Phoenix
Ave. Duration
7h 55m
When
Every day
Estimated price
$220 - $600
Train operators
Amtrak

Amtrak is a rail service that connects the US and three Canadian provinces. Covering 21,000 route miles (34,000km) Amtrak operates more than 300 trains daily. These medium and long distance intercity services operate at speeds of up to 240km/h, to more than 500 destinations. Founded in 1971, it is based in Washington, D.C. and offers four classes of travel: First Class, Sleeper, Business and Coach. Ticket fares are divided into five subclasses: Saver, Value, Flexible, Business and Premium. Amtrak trains are known for their wide seats, plug-in power, big windows and storage capabilities.

Rome2rio's guide to Amtrak
Contact Details
Phone
+1 215-856-7924
Website
amtrak.com
Train from Chicago Union Station to Portland Union Station
Ave. Duration
45h 55m
Frequency
Twice daily
Estimated price
$200 - $290
Website
amtrak.com
Coach Seat
$200 - $290
Premium
$500 - $750
Flexi Coach Seat
$420 - $650
Business Seat
$460 - $650
Bus operators
Pacific Crest Buslines Bend
Phone
+1 541-923-1732 / 541-344-6265
Website
pacificcrestbuslines.com
Bus from Eugene Greyhound Station to Hawthorne Station Bend
Ave. Duration
2h 30m
Frequency
Once daily
Estimated price
$40 - $55
Schedules at
pacificcrestbuslines.com
Central Oregon Breeze
Website
cobreeze.com
Bus from Portland International Airport to Redmond Hub
Ave. Duration
3h 9m
Frequency
Once daily
Estimated price
$40 - $65
Schedules at
cobreeze.com
Economy
$40 - $50
Premium
$50 - $65
Walk On
$50 - $65
Bus from Portland Union Station to Redmond Hub
Ave. Duration
3h 39m
Frequency
Once daily
Estimated price
$40 - $70
Schedules at
cobreeze.com
Economy
$40 - $55
Premium
$55 - $70
Walk On
$55 - $70

Want to know more about travelling around United States

Rome2rio's Travel Guide series provide vital information for the global traveller. Filled with useful and timely travel information, the guides answer all the hard questions - such as 'How do I buy a ticket?', 'Should I book online before I travel? ', 'How much should I expect to pay?', 'Do the trains and buses have Wifi?' - to help you get the most out of your next trip.

More Questions & Answers

The best way to get from Chicago to Chicago O'Hare Airport is to subway which takes 43m and costs $2 - $5.

More details