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Cheap flights from Redmond to Chicago from $190

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Redmond to Chicago departing on 9/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Find the cheapest flights from Redmond to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
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
Fri, Sep 11 - Tue, Sep 15
Delta Logo
7:24 pm - 8:48 am
RDM
-
MDW
11h 24m
2 stops
Delta Logo
9:24 am - 6:44 pm
MDW
-
RDM
11h 20m
2 stops
$464Delta
Thu, Sep 10 - Mon, Sep 14
Delta Logo
7:36 pm - 8:39 am
RDM
-
MDW
11h 03m
2 stops
Delta Logo
1:51 pm - 10:18 pm
MDW
-
RDM
10h 27m
2 stops
$473Delta
Tue, Aug 18 - Sat, Aug 22
Delta Logo
6:20 am - 4:50 pm
RDM
-
MDW
8h 30m
2 stops
Delta Logo
1:00 pm - 11:40 pm
MDW
-
RDM
12h 40m
2 stops
$524Delta
Wed, Oct 7 - Mon, Oct 12
Delta Logo
6:20 am - 4:50 pm
RDM
-
MDW
8h 30m
2 stops
Delta Logo
1:00 pm - 11:40 pm
MDW
-
RDM
12h 40m
2 stops
$556Delta
Wed, Oct 7 - Mon, Oct 12
Delta Logo
7:25 pm - 9:14 am
RDM
-
MDW
11h 49m
2 stops
Delta Logo
12:41 pm - 10:57 pm
MDW
-
RDM
12h 16m
2 stops
$579Delta
Fri, Jul 3 - Wed, Jul 8
Delta Logo
6:20 am - 4:50 pm
RDM
-
MDW
8h 30m
2 stops
Delta Logo
1:00 pm - 11:40 pm
MDW
-
RDM
12h 40m
2 stops
$598Delta
Wed, Oct 7 - Mon, Oct 12
Delta Logo
7:36 pm - 8:39 am
RDM
-
MDW
11h 03m
2 stops
Delta Logo
9:24 am - 6:45 pm
MDW
-
RDM
11h 21m
2 stops
$626Delta
Thu, Aug 20 - Sun, Aug 23
Delta Logo
6:20 am - 10:10 pm
RDM
-
MDW
13h 50m
2 stops
Delta Logo
1:00 pm - 10:46 pm
MDW
-
RDM
11h 46m
2 stops
$641Delta
Wed, Oct 7 - Sat, Oct 10
Delta Logo
6:20 am - 10:10 pm
RDM
-
MDW
13h 50m
2 stops
Delta Logo
1:00 pm - 11:40 pm
MDW
-
RDM
12h 40m
2 stops
$700Delta
Wed, Oct 7 - Mon, Oct 12

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Delta flights from Redmond to Chicago Midway Airport

Our best Delta deals on Redmond to Chicago Midway Airport flight tickets
Delta
Sep 11
RDM7:24 pmBend/Redmond
11h 24m
2 stops
MDW8:48 amChicago Midway
Sep 15
MDW1:47 pmChicago Midway
11h 21m
2 stops
RDM11:08 pmBend/Redmond
$389
Delta
Sep 10
RDM7:24 pmBend/Redmond
11h 24m
2 stops
MDW8:48 amChicago Midway
Sep 14
MDW9:24 amChicago Midway
11h 20m
2 stops
RDM6:44 pmBend/Redmond
$464
Delta
Aug 18
RDM7:36 pmBend/Redmond
11h 03m
2 stops
MDW8:39 amChicago Midway
Aug 22
MDW1:51 pmChicago Midway
10h 27m
2 stops
RDM10:18 pmBend/Redmond
$473

momondo Fare Finder

 
Customize your flight search to find flights from Redmond to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated June 23, 2026.
Use the filters below to find and compare flights from Redmond to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Fri 9/11

7:24 pm-8:48 am

2 stops11h 24m

Chicago Midway

Tue 9/15

1:47 pm-11:08 pm

2 stops11h 21m

$389

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Thu 9/10

7:24 pm-8:48 am

2 stops11h 24m

Chicago Midway

Mon 9/14

9:24 am-6:44 pm

2 stops11h 20m

$464

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Tue 8/18

7:36 pm-8:39 am

2 stops11h 03m

Chicago Midway

Sat 8/22

1:51 pm-10:18 pm

2 stops10h 27m

$473
Quickest round-trip

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Wed 10/7

6:20 am-4:50 pm

2 stops8h 30m

Chicago Midway

Mon 10/12

1:00 pm-11:40 pm

2 stops12h 40m

$524

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Wed 10/7

6:20 am-4:50 pm

2 stops8h 30m

Chicago Midway

Mon 10/12

1:00 pm-11:40 pm

2 stops12h 40m

$556

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Fri 7/3

7:25 pm-9:14 am

2 stops11h 49m

Chicago Midway

Wed 7/8

12:41 pm-10:57 pm

2 stops12h 16m

$579

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Wed 10/7

6:20 am-4:50 pm

2 stops8h 30m

Chicago Midway

Mon 10/12

1:00 pm-11:40 pm

2 stops12h 40m

$598

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Thu 8/20

7:36 pm-8:39 am

2 stops11h 03m

Chicago Midway

Sun 8/23

9:24 am-6:45 pm

2 stops11h 21m

$626

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Wed 10/7

6:20 am-10:10 pm

2 stops13h 50m

Chicago Midway

Sat 10/10

1:00 pm-10:46 pm

2 stops11h 46m

$641

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Wed 10/7

6:20 am-10:10 pm

2 stops13h 50m

Chicago Midway

Mon 10/12

1:00 pm-11:40 pm

2 stops12h 40m

$700

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Redmond to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest airline that flies from Bend/Redmond to Chicago Midway?

Delta is the most popular carrier operating from Bend/Redmond to Chicago Midway

When to book flights from Redmond to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Redmond to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Redmond to Chicago Midway Airport (RDM to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Redmond to Chicago Midway Airport

Fastest flight time

8h 30m

Direct flights

None
The fastest flight from Redmond to Chicago Midway Airport takes 8h 30m
There are no direct flights from Redmond to Chicago Midway Airport. There are no popular flight routes from Redmond to Chicago Midway Airport.
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Frequently asked questions about flying from Redmond to Chicago Midway Airport

  • How far is Bend/Redmond to Chicago Midway by plane?

    A flight from Bend/Redmond to Chicago Midway will travel around 1684.2 mi. In terms of flight time, this usually takes a little over 8h 30m.

  • When did momondo last update prices for flights from Bend/Redmond Airport to Chicago Midway Airport?

    Prices for flights from Bend/Redmond Airport to Chicago Midway Airport were last updated today.

  • How old do you have to be to fly from Bend/Redmond Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Bend/Redmond Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Benton Harbor
Portage
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Crown Point
Chesterton
Monticello
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Redmond to Chicago?

Finding the right flight to Chicago from Redmond is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Chicago quick and easy, saving you time and money.

Can I find flights from Redmond to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Redmond which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Redmond to Chicago?

Once all potential Redmond to Chicago flight options are in front of you, momondo lets you sort and filter flights based on preferences such as airline, price and flight times amongst many other options.

I’m not ready to book a flight from Redmond to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Redmond. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago Midway Airport trip

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