$121 Cheap flight deals from Bend (RDM) to Chicago (CHI)

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This Weekend's Flight Deals from Bend to Chicago

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Jun 21 - Thu, Jul 4
RDM
Robert's Field
ORD
O'Hare Intl.
$593 Roundtrip, found 4 days ago
$593
Roundtrip
found 4 days ago
Select Alaska Airlines flight, departing Fri, Jun 21 from Robert's Field to O'Hare Intl., returning Thu, Jul 4, priced at $593 found 4 days ago

Airfares from $121 One Way, $242 Round Trip from Bend to Chicago

Prices starting at $242 for return flights and $121 for one-way flights to Chicago were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Tue, Oct 15 - Sat, Oct 26
RDM
Redmond
ORD
Chicago
$242 Roundtrip, found 3 days ago
$242
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Tue, Oct 15 from Redmond to Chicago, returning Sat, Oct 26, priced at $242 found 3 days ago
Tue, Oct 15 - Sat, Oct 26
RDM
Redmond
ORD
Chicago
$243 Roundtrip, found 3 days ago
$243
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Tue, Oct 15 from Redmond to Chicago, returning Sat, Oct 26, priced at $243 found 3 days ago
Wed, Sep 18 - Tue, Sep 24
RDM
Redmond
ORD
Chicago
$243 Roundtrip, found 5 days ago
$243
Roundtrip
found 5 days ago
Select Delta flight, departing Wed, Sep 18 from Redmond to Chicago, returning Tue, Sep 24, priced at $243 found 5 days ago
Tue, Oct 15 - Sat, Oct 26
RDM
Redmond
ORD
Chicago
$247 Roundtrip, found 3 days ago
$247
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Tue, Oct 15 from Redmond to Chicago, returning Sat, Oct 26, priced at $247 found 3 days ago
Sat, Oct 19 - Fri, Oct 25
RDM
Redmond
ORD
Chicago
$252 Roundtrip, found 3 days ago
$252
Roundtrip
found 3 days ago
Select Alaska Airlines flight, departing Sat, Oct 19 from Redmond to Chicago, returning Fri, Oct 25, priced at $252 found 3 days ago

Chicago economy flight packages

Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Downtown Magnificent Mile
4.0-star property

Chicago Marriott Downtown Magnificent Mile

8.4/10 Very Good! (1,006 reviews)

Aug 2 - Aug 4

2 night stay

Redmond (RDM) to Chicago (ORD)

Delta • Non-stop • Coach

Chicago (ORD) to Redmond (RDM)

American Airlines • Non-stop • Coach
per person
found 13 hours ago
This property was very nice and there were eating options and a great bar/lounge.

Reviewed on Apr 22, 2024

Trump International Hotel & Tower Chicago
5.0-star property

Trump International Hotel & Tower Chicago

9.2/10 Wonderful! (1,212 reviews)

Aug 2 - Aug 4

2 night stay

Redmond (RDM) to Chicago (ORD)

Delta • Non-stop • Coach

Chicago (ORD) to Redmond (RDM)

American Airlines • Non-stop • Coach
per person
found 13 hours ago
Everything was outstanding

Reviewed on Apr 2, 2024

Hyatt Place Chicago/Downtown - The Loop
3.0-star property

Hyatt Place Chicago/Downtown - The Loop

8.4/10 Very Good! (1,005 reviews)

Aug 2 - Aug 4

2 night stay

Redmond (RDM) to Chicago (ORD)

Delta • Non-stop • Coach

Chicago (ORD) to Redmond (RDM)

American Airlines • Non-stop • Coach
per person
found 13 hours ago
The parking was down and across the street 1/2 block. Trying to drop off my son who is in a wheelchair and all of his belongings was challenging because the front entry was right at the curb to the busy street. Maybe this is normal in a city?

Reviewed on Jun 15, 2024

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More About Flying To Chicago from Bend

Route Information for Flights from Bend to Chicago

Origin Airport IATA Code
RDM
Destination Airport IATA Code
CHI
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Bend to Chicago

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Frequently asked questions

What is the shortest flight from Bend to Chicago?
Traveling from Roberts Field to Chicago, IL (ORD-O’Hare Intl.) takes at least 4 hours and 41 minutes. Indulge in a tipple and watch a movie or two — this is a great opportunity to sit back and chill out.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on Orbitz.com from January to December 2021. Savings are subject to change based on departure location, date and destination.

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.