RDM - CHI

$189 Find Cheap Flights from Redmond to Chicago - Compare and Save

1 adult
1 adult, Economy, 0 bags

Save 25% or more on flights. Compare deals from all over the web.

Never overpay with our price tracking tools.

Filter searches by price, airline and more to find your best flights.

Everything you should know

Cheapest round-trip
$454
Typical prices: $386-$577
Alaska Airlines
Fri 3/2Tue 3/6
RDM - ORD • 2 stops
Cheapest one-way
$189
Typical prices: $191-$331
Multiple Airlines
Fri 11/16
RDM - ORD • 3 stops
Nonstop flights
Not available
There are currently no direct flights between Redmond and Chicago. You'll need to take a connecting flight to reach the destination.
Insights
Insights
When to travel
May
Cheapest • 22% price drop
May
Most popular
Good to know
+1
Good to know
+1
Top layover airports
Salt Lake City (SLC)
Cheapest • Avg $367 (round-trip)
Portland (PDX)
Shortest trip • 6h 21m (one-way)
Insights
Insights
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to Chicago!
Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Redmond to Chicago (RDM-CHI)

 
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Redmond to Chicago

Tue, Mar 2 - Sat, Mar 6
Alaska Airlines Logo
7:00 am - 11:59 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
14h 59m2 stops Los Angeles Seattle/Tacoma Intl
Alaska Airlines Logo
5:55 pm - 12:17 amORD  Chicago O'Hare Intl-RDM Bend/Redmond
8h 22m1 stop Seattle/Tacoma Intl
$454Alaska Airlines
Thu, Jan 21 - Tue, Jan 26
Alaska Airlines Logo
5:15 am - 1:13 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
5h 58m1 stop Portland
Alaska Airlines Logo
8:00 am - 11:00 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
17h 00m2 stops Seattle/Tacoma Intl Los Angeles
$475Alaska Airlines
Tue, Mar 2 - Sat, Mar 6
United Airlines Logo
1:55 pm - 11:27 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
7h 32m1 stop San Francisco
United Airlines Logo
4:20 pm - 9:28 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
7h 08m1 stop Denver Intl
$475United Airlines
Tue, Nov 17 - Tue, Nov 24
United Airlines Logo
5:00 am - 1:29 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
6h 29m1 stop Denver Intl
United Airlines Logo
4:01 pm - 10:57 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
8h 56m1 stop San Francisco
$475United Airlines
Tue, Dec 1 - Wed, Dec 9
Alaska Airlines Logo
5:20 am - 1:10 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
5h 50m1 stop Portland
Alaska Airlines Logo
5:29 pm - 11:46 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
8h 17m1 stop Seattle/Tacoma Intl
$475Alaska Airlines
Tue, Dec 1 - Wed, Dec 9
Delta Logo
1:23 pm - 11:57 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
8h 34m1 stop Seattle/Tacoma Intl
Delta Logo
2:41 pm - 11:59 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
11h 18m2 stops Detroit Metropolitan Wayne County Salt Lake City
$480Delta
Tue, Dec 1 - Wed, Dec 9
Delta Logo
7:40 pm - 9:37 amRDM  Bend/Redmond-MDW Chicago Midway
11h 57m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County
Delta Logo
12:39 pm - 11:59 pmMDW  Chicago Midway-RDM Bend/Redmond
13h 20m2 stops Minneapolis St Paul Salt Lake City
$485Delta
Tue, Dec 1 - Wed, Dec 9
Delta Logo
7:40 pm - 7:59 amRDM  Bend/Redmond-ORD Chicago O'Hare Intl
10h 19m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County
Delta Logo
3:47 pm - 11:01 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
9h 14m2 stops Minneapolis St Paul Seattle/Tacoma Intl
$485Delta
Wed, Nov 4 - Sat, Nov 7
American Airlines Logo
5:05 am - 2:43 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
7h 38m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
5:00 am - 1:17 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
10h 17m1 stop Phoenix Sky Harbor Intl
$551American Airlines
Sat, Nov 14 - Mon, Nov 16
United Airlines Logo
1:02 pm - 10:46 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
7h 44m1 stop Denver Intl
United Airlines Logo
7:00 am - 1:03 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
8h 03m1 stop Denver Intl
$559United Airlines
Booking Insights

Price, demand and travel trends for Redmond to Chicago flights

Use KAYAK data on prices, travel dates, airlines and seasonal trends to compare options and book flights with more confidence.

How much is a round-trip flight from Redmond to Chicago?

Round-trip flights from Redmond to Chicago typically range from $386 to $577. The lowest price found in the past 5 days was $454, on Alaska Airlines.

What is the cheapest Redmond to Chicago flight route?

There's little price difference between Redmond to Chicago routes. They average around $473 round-trip, based on KAYAK data over the past 12 months.

What's the cheapest day of the week to fly from Redmond to Chicago?

Based on deals KAYAK users found in the last 12 months, Thursday is the cheapest day of the week to fly from Redmond to Chicago. It’s 15% cheaper than the average day, while Monday is the most expensive, with prices 37% higher.

What’s the cheapest month to fly from Redmond to Chicago?

•May and December are the cheapest months to fly from Redmond to Chicago at $367 round-trip.
•October ($592) and February ($572) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 61% on average.
This is based on KAYAK aggregated and averaged internal data over the past 12 months.

Find deals

Key details for Redmond to Chicago flights

Low season

January

Cheapest flight

$189
Beat the crowds with an average 52% drop in travelers.
The most popular month to fly with an average 52% increase in travelers.
One-way flight from Redmond to Chicago O'Hare Intl Airport

When to book flights from Redmond to Chicago

Are your dates flexible? Find out the best times to travel from Redmond to Chicago based on our flight data from the last year. Discover the cheapest month and even day to fly.
Estimated round-trip price

Your Redmond to Chicago flight questions, answered

Find helpful answers about this route, including flight times, airports, airlines and booking tips.

  • What cabin classes can I book on flights from Redmond to Chicago?

    Two cabin classes are available on flights from Redmond to Chicago:

    • Economy Class
    • First Class

  • How long is a flight from Redmond to Chicago?

    A nonstop flight from Redmond to Chicago takes 00m, covering 1,687 miles.

  • Do I need a passport to fly from Redmond to Chicago?

    No, a passport is not required for this domestic route, but you will need a real ID-compliant driver's license, a state ID or another TSA-accepted form of identification.

  • How much should I expect to pay for a Redmond to Chicago flight?

    Round-trip flights from Redmond to Chicago range from $386 to $577, with an average of $473 over the past 12 months. Anything below $386 counts as a good deal.

  • Have flight prices from Redmond to Chicago changed much recently?

    Yes. Based on fares seen in the past 5 days, round-trip prices on this route showed a wide range, from about $454 to $2,895. That means the highest observed fare was about 6x higher than the lowest one.

  • How are flight prices from Redmond to Chicago looking right now?

    One-way fares from Redmond to Chicago are currently higher than usual. Average one-way flight prices are about $395, which is 48% above the typical average for this route.

  • What car rental options are available in Chicago?

    Since Chicago is served by multiple airports, car rental options and rates can vary depending on which one you fly into.
    Near Chicago O'Hare Intl Airport (ORD) — daily rates from around $17:

    • Routes Car & Truck Rentals
    • Europcar
    • Hertz
    • Ace
    • Dollar

    Near Chicago Midway Airport (MDW) — daily rates from around $32:

    • Hertz
    • Dollar
    • Budget
    • Alamo
    • Rent-A-Wreck

    Near Chicago Greater Rockford Airport (RFD) — daily rates from around $28:

    • Alamo
    • Enterprise Rent-A-Car
    • Budget
    • Avis
    • National

  • Which airports can I use when flying from Redmond to Chicago?

    Flights from Redmond to Chicago usually depart from Bend/Redmond (RDM) and may arrive at several airports in Chicago area, including Chicago Midway (MDW), Chicago O'Hare Intl (ORD) and Chicago Greater Rockford (RFD).

  • Which airports do connecting flights from Redmond to Chicago pass through?

    One-stop flights from Redmond to Chicago most commonly connect through:

    • Seattle/Tacoma Intl (SEA) - 38% of one-stop connections
    • Denver Intl (DEN) - 17% of one-stop connections
    • Salt Lake City (SLC) - 15% of one-stop connections
    • Portland (PDX) - 12% of one-stop connections

  • Can I save money by using flexible dates for flights from Redmond to Chicago?

    Yes. Flexible dates can save you up to 38% on flights from Redmond to Chicago. Thursday is the cheapest departure day at $406 round-trip on average, while Monday is the most expensive at $650, a difference of $244.

    KAYAK's flexible dates feature shows options up to 3 days before and after your selected dates, making it easier to compare nearby fares.

  • How much time can I save by choosing a different layover airport from Redmond to Chicago?

    Flying via Portland (PDX) gives the shortest average 1-stop total travel time at 6h 21m, compared with 6h 39m via Salt Lake City (SLC) and 6h 54m via Denver Intl (DEN).

  • What is the time difference between Redmond and Chicago?

    Chicago is 2 hours ahead of Redmond (Central Time vs Pacific Time). Plan for the time shift when scheduling connections or first-day activities.

  • What popular places can I visit in Chicago?

    Some of the most popular sights in Chicago are Magnificent Mile, Grant Park and Soldier Field. These are among the most viewed places in Chicago on KAYAK.

Your guide to booking Redmond to Chicago flights

Get tips on when to book, when to fly and what to know before your trip.
  • If your dates are flexible, aim for a Thursday departure and avoid flying on Monday. On this route, Thursday flights average $406, about $244 less than Monday fares (38% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Redmond to Chicago trip for May. Fares historically average $367 round-trip in that month - typically $225 less than the most expensive month, which is October (based on the last 12 months).
  • If you're arriving late at night and need somewhere to stay, check out these hotels close to Chicago Midway Airport.

    • DoubleTree by Hilton Chicago Midway Airport
    • Holiday Inn Chicago - Midway Airport S by IHG
    • Skylark Motel

More options for your flight from Redmond to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Car rentals in Chicago
Hotels in Chicago
Vacations in Chicago