RDM - CHI

$187 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
$435
Typical prices: $369-$532
United Airlines
Sun 11/18Sat 12/8
RDM - ORD • 1 stop
Cheapest one-way
$187
Typical prices: $165-$335
Multiple Airlines
Fri 10/5
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
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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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

Wed, Nov 18 - Tue, Dec 8
United Airlines Logo
2:05 pm - 11:27 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
7h 22m1 stop San Francisco
United Airlines Logo
6:00 am - 11:51 amORD  Chicago O'Hare Intl-RDM Bend/Redmond
7h 51m1 stop San Francisco
$435United Airlines
Tue, Sep 22 - Sat, Sep 26
Alaska Airlines Logo
1:33 pm - 1:22 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
21h 49m1 stop San Diego
Alaska Airlines Logo
7:00 pm - 11:58 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
6h 58m1 stop Seattle/Tacoma Intl
$435Alaska 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
$435Alaska Airlines
Sat, Sep 12 - Wed, Sep 23
Alaska Airlines Logo
6:17 pm - 6:20 amRDM  Bend/Redmond-ORD Chicago O'Hare Intl
10h 03m1 stop Seattle/Tacoma Intl
Alaska Airlines Logo
7:00 pm - 11:58 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
6h 58m1 stop Seattle/Tacoma Intl
$435Alaska Airlines
Sat, Sep 12 - Wed, Sep 23
Delta Logo
1:44 pm - 11:57 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
8h 13m1 stop Seattle/Tacoma Intl
Delta Logo
8:55 am - 6:44 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
11h 49m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl
$440Delta
Sat, Sep 12 - Wed, Sep 23
Delta Logo
7:24 pm - 7:56 amRDM  Bend/Redmond-ORD Chicago O'Hare Intl
10h 32m2 stops Seattle/Tacoma Intl Detroit Metropolitan Wayne County
Delta Logo
5:44 pm - 11:08 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
7h 24m1 stop Seattle/Tacoma Intl
$440Delta
Tue, Sep 1 - Sat, Sep 5
United Airlines Logo
7:30 am - 4:36 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
7h 06m1 stop San Francisco
United Airlines Logo
12:51 pm - 6:28 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
7h 37m1 stop San Francisco
$473United Airlines
Wed, Sep 2 - Tue, Sep 15
United Airlines Logo
1:03 pm - 9:29 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
6h 26m1 stop Denver Intl
United Airlines Logo
2:32 pm - 9:11 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
8h 39m1 stop Denver Intl
$473United Airlines
Mon, Sep 28 - Wed, Sep 30
American Airlines Logo
2:46 pm - 12:30 amRDM  Bend/Redmond-ORD Chicago O'Hare Intl
7h 44m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
1:45 pm - 7:05 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
7h 20m1 stop Phoenix Sky Harbor Intl
$481American Airlines
Fri, Nov 27 - Tue, Dec 1
American Airlines Logo
1:47 pm - 11:34 pmRDM  Bend/Redmond-ORD Chicago O'Hare Intl
7h 47m1 stop Phoenix Sky Harbor Intl
American Airlines Logo
3:13 pm - 11:56 pmORD  Chicago O'Hare Intl-RDM Bend/Redmond
10h 43m1 stop Phoenix Sky Harbor Intl
$548American 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 from Redmond to Chicago with more confidence.

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

Round-trip flights from Redmond to Chicago start at $435. Prices are typical for this route right now, with typical round-trip fares ranging from $369 to $532. The lowest price found in the past 5 days was $435 on United 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?

Sunday is the cheapest day of the week to fly from Redmond to Chicago, it is 18% cheaper than the average day. Monday is the most expensive day with flight prices 28% higher than average. Based on deals found by KAYAK users in the last 12 months.

What is 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

$187
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 18% lower on average.
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 route details based on KAYAK data, including flight times, airports, airlines and booking questions.

  • 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).

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

    Only Economy Class is available on flights from Redmond to Chicago.

  • 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

    Seattle/Tacoma Intl (SEA) handles the largest share of one-stop connections on this route.

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

    On the Redmond to Chicago route, being flexible with your departure day can save you up to 36%. Sunday is the cheapest day at $368 round-trip on average, while Monday is the most expensive at $572: a $204 difference. Cheaper weekend fares like these are typical of routes dominated by weekday business travel.

  • What popular places can I visit in Chicago?

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

  • How long is a flight from Redmond to Chicago?

    A nonstop flight from Redmond to Chicago takes 0h 00m, covering 1,687 miles.

  • What are the earliest and latest flights from Redmond to Chicago?

    These are the earliest and latest flight times available from Redmond to Chicago:

    • Earliest: departs at 12:00 am and lands at 12:00 am
    • Latest: departs at 12:00 am and lands at 12:00 am.

    The flight takes about 0h 00m.

  • 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.

  • 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 $435 to $2,057. That means the highest observed fare was about 5x 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 lower than usual. Average one-way flight prices are about $210, which is 16% below the typical average for this route.

  • 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 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

  • 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.

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 can be flexible, aim for a Sunday departure instead of Monday. On this route, Sunday flights average $368 - about $204 less than Monday (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

Everything you need to know for your flight from Redmond to Chicago

Information on your arrival and departure airports

Redmond (RDM)