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RDM - CHI

$266 Find Cheap Flights from Redmond to Chicago - Compare and Save

1 adult
1 adult, Economy, 0 bags

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Everything you should know

Cheapest round-trip
$417
Typical prices: $386-$577
Alaska Airlines
Sat 12/8Sun 12/9
RDM - ORD • 2 stops
Cheapest one-way
$266
Typical prices: $191-$331
United Airlines
Sat 10/20
RDM - ORD • 1 stop
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 23m (one-way)
Insights
Insights
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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

Mon, Nov 16 - Thu, Nov 19
Multiple Airlines Logo
12:20 pm - 5:13 amRDM  Bend/Redmond-ORD Chicago O'Hare Intl
14h 53m1 stop Las Vegas Harry Reid Intl
Multiple Airlines Logo
6:30 am - 11:40 amORD  Chicago O'Hare Intl-RDM Bend/Redmond
31h 10m2 stops Denver Intl Las Vegas Harry Reid Intl
$384Multiple Airlines
Wed, Dec 9 - Sat, Dec 12
Alaska Airlines Logo
6:16 am - 11:59 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
15h 43m2 stops Los Angeles Seattle/Tacoma Intl
Alaska Airlines Logo
5:46 pm - 11:46 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
8h 00m1 stop Seattle/Tacoma Intl
$424Alaska Airlines
Mon, Nov 16 - Thu, Nov 19
Multiple Airlines Logo
12:20 pm - 5:13 amRDM  Bend/Redmond-ORD Chicago O'Hare Intl
14h 53m1 stop Las Vegas Harry Reid Intl
Multiple Airlines Logo
5:15 pm - 11:40 amORD  Chicago O'Hare Intl-RDM Bend/Redmond
20h 25m1 stop Las Vegas Harry Reid Intl
$437Multiple Airlines
Mon, Nov 2 - Thu, Nov 5
Multiple Airlines Logo
12:20 pm - 5:13 amRDM  Bend/Redmond-ORD Chicago O'Hare Intl
14h 53m1 stop Las Vegas Harry Reid Intl
Multiple Airlines Logo
5:15 pm - 11:40 amORD  Chicago O'Hare Intl-RDM Bend/Redmond
20h 25m1 stop Las Vegas Harry Reid Intl
$454Multiple Airlines
Tue, Nov 3 - Sat, Nov 7
United Airlines Logo
2:05 pm - 11:27 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
7h 22m1 stop San Francisco
United Airlines Logo
3:56 pm - 9:18 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
7h 22m1 stop Denver Intl
$455United Airlines
Wed, Nov 11 - Sat, Nov 14
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
$455United Airlines
Sat, Jan 16 - Wed, Jan 20
Alaska Airlines Logo
5:15 am - 1:13 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
5h 58m1 stop Portland
Alaska Airlines Logo
3:19 pm - 8:55 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
7h 36m1 stop Seattle/Tacoma Intl
$455Alaska Airlines
Wed, Nov 11 - Sat, Nov 14
Delta Logo
1:20 pm - 11:59 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
8h 39m1 stop Seattle/Tacoma Intl
Delta Logo
3:47 pm - 10:57 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
9h 10m2 stops Minneapolis St Paul Seattle/Tacoma Intl
$460Delta
Tue, Nov 3 - Sat, Nov 7
Delta Logo
12:25 pm - 10:05 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
7h 40m1 stop Salt Lake City
Delta Logo
3:30 pm - 10:02 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
8h 32m2 stops Minneapolis St Paul Salt Lake City
$460Delta
Sat, Jan 16 - Wed, Jan 20
Alaska Airlines Logo
2:41 pm - 11:59 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
7h 18m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
8:00 am - 2:01 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
8h 01m1 stop Seattle/Tacoma Intl
$487Alaska 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 $417, 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 $445 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

$266
Beat the crowds with an average 79% drop in travelers.
The most popular month to fly with an average 50% 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 $417 to $1,236. That means the highest observed fare was about 3x 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 $557, which is 109% 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
    • Dollar
    • Ace

    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 $30:

    • 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) - 42% of one-stop connections
    • Denver Intl (DEN) - 19% of one-stop connections
    • Salt Lake City (SLC) - 15% of one-stop connections
    • Portland (PDX) - 10% 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 23m, 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