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RDM - CHI

$179 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
$409
Typical prices: $369-$532
Multiple Airlines
Mon 1/8Wed 1/10
RDM - ORD • 1 stop
Cheapest one-way
$179
Typical prices: $165-$335
Multiple Airlines
Fri 10/26
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
November
Cheapest • 28% 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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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

Fri, Jan 8 - Sun, Jan 10
Multiple Airlines Logo
12:20 pm - 6:10 amRDM  Bend/Redmond-ORD Chicago O'Hare Intl
15h 50m1 stop Las Vegas Harry Reid Intl
Multiple Airlines Logo
7:30 am - 11:40 amORD  Chicago O'Hare Intl-RDM Bend/Redmond
30h 10m1 stop Las Vegas Harry Reid Intl
$409Multiple Airlines
Wed, Oct 28 - Wed, Nov 4
Alaska Airlines Logo
1:35 pm - 5:40 amRDM  Bend/Redmond-ORD Chicago O'Hare Intl
14h 05m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
2:07 pm - 11:24 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
11h 17m2 stops Portland Los Angeles
$414Alaska Airlines
Wed, Dec 2 - Sat, Dec 12
Delta Logo
6:21 am - 11:59 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
15h 38m2 stops Seattle/Tacoma Intl Los Angeles
Delta Logo
6:40 am - 12:43 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
8h 03m1 stop Seattle/Tacoma Intl
$424Delta
Wed, Dec 2 - Wed, Dec 9
Delta Logo
6:21 am - 11:59 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
15h 38m2 stops Seattle/Tacoma Intl Los Angeles
Delta Logo
5:55 pm - 11:01 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
7h 06m1 stop Seattle/Tacoma Intl
$424Delta
Tue, Jan 19 - Sat, Jan 23
Alaska Airlines Logo
10:28 am - 11:59 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
11h 31m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
2:11 pm - 11:00 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
10h 49m2 stops Portland Los Angeles
$424Alaska 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
$452Multiple Airlines
Tue, Jan 19 - Sat, Jan 23
United Airlines Logo
1:07 pm - 9:31 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
6h 24m1 stop Denver Intl
United Airlines Logo
12:40 pm - 5:45 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
7h 05m1 stop San Francisco
$455United Airlines
Wed, Oct 28 - Wed, Nov 4
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
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
6:30 am - 11:40 amORD  Chicago O'Hare Intl-RDM Bend/Redmond
31h 10m2 stops Denver Intl Las Vegas Harry Reid Intl
$466Multiple Airlines
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.

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, Sunday is the cheapest day of the week to fly from Redmond to Chicago. It’s 18% cheaper than the average day, while Monday is the most expensive, with prices 28% higher.

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

•November is the cheapest month to fly from Redmond to Chicago at $320 round-trip.
•February ($572) and June ($503) are the most expensive months.
•The price difference between flying in the cheapest and most expensive months is 78% 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

$179
Beat the crowds with an average 71% drop in travelers.
The most popular month to fly with an average 51% 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 $369 to $532, with an average of $445 over the past 12 months. Anything below $369 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 $409 to $1,023. 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 in line with typical prices for this route. Average one-way fares are about $255.

  • 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 36% on flights from Redmond to Chicago. Sunday is the cheapest departure day at $368 round-trip on average, while Monday is the most expensive at $572, a difference of $204.

    Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • 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 Sunday departure and avoid flying on Monday. On this route, Sunday flights average $368, about $204 less than Monday fares (36% savings) based on the last 12 months.
  • If you can choose when to travel, plan your Redmond to Chicago trip for November. Fares historically average $320 round-trip in that month - typically $252 less than the most expensive month, which is February (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