RDM - CHI

$185 Find Cheap Flights from Redmond to Chicago - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Redmond to Chicago departing on 7/11. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Chicago

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Redmond to Chicago, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Redmond to Chicago, as well as popular online travel agencies
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

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Everything you should know

Cheapest round-trip
$367
Typical prices: $451-$917
Delta
Fri 7/3Wed 7/8
RDM - ORD • 1 stop
Cheapest one-way
$185
Typical prices: $161-$359
Alaska Airlines
Sat 7/11
RDM - ORD • 1 stop
Top airlines
Cheapest • from $367 (round-trip)
Best reviews • 7.9 score
Airline reviews
Airline reviews
+1
+1
Airline reviews
Airline reviews
+1
Nonstop flights
Not available
There are currently no direct flights between Redmond and Chicago. You'll need at least 1 connection.
Insights
Insights
Insights
Insights
Top layover airports
Cheapest • Avg $346 (round-trip)
Shortest trip • 6h 01m (one-way)
Insights
Insights
Insights
Insights
When to travel
Cheapest • 25% price drop
Most popular
Good to know
Good to know
+1
+1
Good to know
Good to know
+1
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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)

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Redmond to Chicago that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Redmond to Chicago

Fri, Jul 3 - Wed, Jul 8
Delta Logo
1:25 pm - 11:39 pm
RDM
-
ORD
8h 14m
1 stop
Delta Logo
1:00 pm - 6:43 pm
ORD
-
RDM
7h 43m
1 stop
$367Delta
Wed, Jul 15 - Tue, Jul 21
Alaska Airlines Logo
7:49 pm - 5:00 am
RDM
-
ORD
7h 11m
1 stop
Alaska Airlines Logo
8:20 pm - 9:04 am
ORD
-
RDM
14h 44m
1 stop
$369Alaska Airlines
Fri, Jul 3 - Wed, Jul 8
Delta Logo
6:26 am - 9:57 pm
RDM
-
ORD
13h 31m
2 stops
Delta Logo
1:00 pm - 6:43 pm
ORD
-
RDM
7h 43m
1 stop
$372Delta
Wed, Jul 15 - Tue, Jul 21
Delta Logo
1:27 pm - 11:38 pm
RDM
-
ORD
8h 11m
1 stop
Delta Logo
2:02 pm - 10:57 pm
ORD
-
RDM
10h 55m
2 stops
$374Delta
Fri, Sep 11 - Tue, Sep 15
Delta Logo
1:44 pm - 11:57 pm
RDM
-
ORD
8h 13m
1 stop
Delta Logo
12:50 pm - 6:44 pm
ORD
-
RDM
7h 54m
1 stop
$379Delta
Fri, Sep 11 - Tue, Sep 15
Delta Logo
7:24 pm - 8:38 am
RDM
-
ORD
11h 14m
2 stops
Delta Logo
7:40 pm - 11:47 pm
ORD
-
RDM
6h 07m
1 stop
$384Delta
Thu, Sep 10 - Mon, Sep 14
Delta Logo
1:44 pm - 11:57 pm
RDM
-
ORD
8h 13m
1 stop
Delta Logo
7:40 pm - 11:47 pm
ORD
-
RDM
6h 07m
1 stop
$389Delta
Fri, Sep 11 - Tue, Sep 15
Delta Logo
7:24 pm - 8:48 am
RDM
-
MDW
11h 24m
2 stops
Delta Logo
1:47 pm - 11:08 pm
MDW
-
RDM
11h 21m
2 stops
$389Delta
Thu, Aug 20 - Sun, Aug 23
Delta Logo
6:15 am - 6:19 pm
RDM
-
ORD
10h 04m
2 stops
Delta Logo
7:48 am - 11:50 am
ORD
-
RDM
6h 02m
1 stop
$394Delta
Fri, Jul 3 - Wed, Jul 8
Delta Logo
1:25 pm - 11:39 pm
RDM
-
ORD
8h 14m
1 stop
Delta Logo
1:00 pm - 6:43 pm
ORD
-
RDM
7h 43m
1 stop
$397Delta
Booking Insights

KAYAK's insights & trends for Redmond to Chicago flights

Get data-powered insights and trends into flights from Redmond to Chicago to help you find the cheapest flights, the best time to fly and much more.

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

This analysis is based on the cheapest round-trip price found on KAYAK in the last 12 months by searching for a flight from Redmond to Chicago departing in July.

What is the cheapest month to fly from Redmond to Chicago?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Redmond to Chicago, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Redmond to Chicago is February, where tickets cost $230 (return) on average. On the other hand, the most expensive months are July and September, where the average cost of round-trip tickets is $378 and $352 respectively.

Good to know

Low seasonJanuary
Cheapest flight$185
Best time to beat the crowds but there is an average 21% increase in price.
Most popular time to fly with an average 1% increase in price.
Flight from Redmond to Chicago O'Hare 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
KAYAK looks at all historical flight data for each date to provide a predicted price for one-way trips or round-trips with a duration up to 40 days. While we try to provide actual minimum prices for each date, some prices are predictions and actual prices may differ.

FAQs for booking flights from Redmond to Chicago

  • What is the cheapest flight from Redmond to Chicago?

    In the last 5 days, the lowest price for a flight from Redmond to Chicago was $185 for a one-way ticket and $367 for a round-trip.

  • Do I need a passport to fly between Redmond and Chicago?

    No, a passport isn't needed to fly from Redmond to Chicago. However, local authorities might ask for an official ID.

  • Which aircraft models fly most regularly from Redmond to Chicago?

    We unfortunately don’t have that data for this specific route.

  • Which airline alliances offer flights from Redmond to Chicago?

    SkyTeam, Star Alliance, and oneworld are the airline alliances operating flights between Redmond and Chicago, with SkyTeam being the most commonly used for this route.

  • Which is the best airline for flights from Redmond to Chicago, Alaska Airlines or Delta?

    The two airlines most popular with KAYAK users for flights from Redmond to Chicago are Alaska Airlines and Delta. With an average price for the route of $456 and an overall rating of 7.9, Alaska Airlines is the most popular choice. Delta is also a great choice for the route, with an average price of $370 and an overall rating of 7.8.

  • How does KAYAK find such low prices on flights from Redmond to Chicago?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Redmond to Chicago.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Redmond to Chicago?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Redmond is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Redmond to Chicago?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Redmond with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Redmond to Chicago?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Redmond up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Redmond to Chicago

 
See real verified KAYAK customer reviews for airlines flying from Redmond to Chicago. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Redmond to Chicago? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
Alaska AirlinesOverall score based on 12560 reviews
8.1Boarding
8.5Crew
7.0Entertainment
7.0Food
7.8Comfort
Airline reviews

Great with American Poor with Alaska airlines. 3 hrs isn’t enough to transfer bags from one gate to another 5-6 gates away in the same terminal. Bags essential for cruise were unavailable Flights delayed cascading the problem. (Alaska Airlines responsibility). Very poor execution of operations that should be the simplest aspect of travel.

4.0 OkayDave, Jun 2026
FSD - ORD
Read more Alaska Airlines reviews

Great with American Poor with Alaska airlines. 3 hrs isn’t enough to transfer bags from one gate to another 5-6 gates away in the same terminal. Bags essential for cruise were unavailable Flights delayed cascading the problem. (Alaska Airlines responsibility). Very poor execution of operations that should be the simplest aspect of travel.

They lost my bag and 24 hours later have yet to find it

When I checked in with full service, requesting a wheelchair, as I had asked for ahead of time, the customer service agent said “wait over there, nothing more. I waited in the designated space for about 40 minutes before learning from another passenger that I needed to check in again at a specific assistance desk. I was early, so I made it on time to my flight. Your agent should not assume I knew anything, which I didn’t. This was all new, in a recently remodeled space. New to me, anyway.

My flight was several times rescheduled and then finally canceled.

Great trip. No complaints. Impressed with the crew’s response to various challenges pre-boarding.

3 of the 4 legs of our trip the crews were awesome! 1 leg the trip attendants were rude & dismissive, didn't even greet us when boarding even though both myself & my husband said hello directly to them when we boarded.

The flight kept getting delayed due to a maintenance issue. That happens, but there is no excuse for changing the gate FIVE TIMES, including one time nearly all the way across SeaTac. After we were delayed for 3+ hours, they did send us (via email) a $12 meal voucher...except you can't find a $12 meal anywhere in that airport, unless you consider a bag of M&M's and a bottle of water a meal. The plane had one problem after another but finally took off 4.5 hours late. This caused us to miss our hotel shuttle at ORD (they didn't run past midnight and it was 3 am) so we had to wait 25 minutes and pay for an Uber. I did get a $50 flight voucher from Alaska...big deal. Barely covers my Uber ride that I shouldn't have needed.

It was good. Too long for older people. Service and support was great! Friendly crew!

We were 35 minutes late because the caterer had not stocked the plane. Plane was fully loaded and ready to go 15 minutes before departure time. We sat there 35 minutes?

Many gate changes in Seattle and mechanical problems on plane which resulted in a new gate change. Both flights, from Seattle to Detroit and Seattle to Eugene resulted in a lot of walking and tram taking.

The flights are constantly late anymore, and they won't even give you a glass of water on the plane. For years, they were able to do a service on this flight from Atlanta to Knoxville and Knoxville Atlanta now they say it's too short of a flight. You can't even get a quick drink of water.

Flight got canceled 4 times, missed my connecting flight due to delays, have to wait to go home tomorrow

Third flight in two months where the crew was not there. Comfort seating does not guarantee overhead bin space. Passengers with children are allowed on the plane first - if you are flying to and from Orlando, this means half the plane has boarded before you get on. And somehow all the bin space is taken up. 3 out of 5 flights have had issues with equipment or procedure. Some of these instances caused the flight to be delayed because of a "nuisance" light. One time it was a bag that had been brought on board but did not belong to anyone so we had to return to the gate. Last night we were told the "AC" on the plane doesn't work well and we're 10th for take off- because the crew was late - and that it will get cool when we're in the air. Not sure if this is usual, but I didn't think flight crew could jump seat in first class. Movie and TV selection has not been refreshed for several months- flying one to two round trips each month easily exhausts the list of content.

Great experience nice pilot very soft and easy landing and take off

We sat on the runway for over an hour before departure. That was unwelcome.

Horrible. Faucet in sink not working, wifi not working. Didn’t bring food or snacks

Flight was delayed before take off and at landing. Baggage took 20 minutes. Flight crew would not serve full soft drink and had to ask multiple times before receiving water.

From checking to boarding, it was a seamless experience. The service agents were so helpful. The flight crew was so pleasant.

Gate agent showed up 20 minutes before boarding and was not at all friendly. Had to take this flight due to the one on the day before being cancelled and any later options were already full with long standby lists. Despite having paid for Delta Comfort seats, Delta did not allow me (or anyone) to choose their seat. The agent assigned them for everyone just prior to boarding. Self seat selection was allowed on the original flight. Flight staff was great - very friendly.

Flight attendants were great. Cheerful, upbeat and friendly. Jet, in particular, was fantastic.

Very easy ! Use the kiosk and bag drop and right to security within 10 min

Over 5 hour delay with minimal updates or ability to standby for alternative flights. During boarding and 1 hr+ wait for takeoff, seats were drenched w water from air conditioning condensation and always leftover crumbs on carpet and seats

Boarded early, left early, arrived 40 mins early! A win win for me!

These airplanes should be illegal. The seats are two tight, it is a safety issue. Wheelchair support was ridiculously slow. We almost missed our flight.

This flight is a quick way to get to Chicago, but a bit expensive.

O’hsre taxi and deboarding took 40 minutes. Needed 20 minutes extra time between connecting flights to avoid running through terminal.

Standard flight with a drinks and a snack- overall very quick flight. The flight attendants were very strict, bordered on rude.

Delayed - weather wasn't bad at either end. Also sat on tarmac in ORD.

boarded early to only find out that flight would sit at gate for 45 min to an hour. Landed in chicago and sat on runway for over an hour before got to gate. Total delay was extensive for a 45 min flight door to door.

The flight was significantly delayed. The inbound flight from EWR was delayed departing because of mechanical problems. My original departure from CLT was 5:28 pm but due to the delay of the inbound flight, after arrival, deplaning, cleaning, boarding, we did not push back from the gate until 9:00 pm. Once in the air, the flight was smooth and what was originally supposed to be an arrival in ORD at 7:30 pm local time turned out to be 9:35 pm.

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

Information on your arrival and departure airports