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Cheap flights from Redmond to Chicago from $245

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 5/30. 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
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
7:20 pm - 8:43 am
RDM
-
MDW
11h 23m
2 stops
Delta Logo
9:22 am - 6:35 pm
MDW
-
RDM
11h 13m
2 stops
$397Delta
Sat, May 23 - Sat, May 30
Delta Logo
5:20 am - 6:18 pm
RDM
-
MDW
10h 58m
2 stops
Delta Logo
1:18 pm - 11:58 pm
MDW
-
RDM
12h 40m
2 stops
$479Delta
Fri, Jul 3 - Wed, Jul 8
Delta Logo
7:20 pm - 8:43 am
RDM
-
MDW
11h 23m
2 stops
Delta Logo
1:22 pm - 10:14 pm
MDW
-
RDM
10h 52m
2 stops
$487Delta
Tue, May 19 - Sat, May 23
Delta Logo
7:25 pm - 8:37 am
RDM
-
MDW
11h 12m
2 stops
Delta Logo
1:49 pm - 11:58 pm
MDW
-
RDM
12h 09m
2 stops
$537Delta
Fri, Jul 3 - Wed, Jul 8
Delta Logo
6:10 am - 6:33 pm
RDM
-
MDW
10h 23m
2 stops
Delta Logo
1:22 pm - 10:54 pm
MDW
-
RDM
11h 32m
2 stops
$540Delta
Wed, May 20 - Wed, May 27
Delta Logo
5:20 am - 6:18 pm
RDM
-
MDW
10h 58m
2 stops
Delta Logo
1:49 pm - 11:58 pm
MDW
-
RDM
12h 09m
2 stops
$579Delta
Fri, Jul 3 - Wed, Jul 8
Delta Logo
7:25 pm - 8:37 am
RDM
-
MDW
11h 12m
2 stops
Delta Logo
6:00 am - 10:58 pm
MDW
-
RDM
18h 58m
2 stops
$586Delta
Fri, Jun 19 - Mon, Jun 22
Delta Logo
5:05 am - 6:33 pm
RDM
-
MDW
11h 28m
2 stops
Delta Logo
1:59 pm - 11:44 pm
MDW
-
RDM
11h 45m
2 stops
$598Delta
Sat, May 30 - Sun, May 31
Delta Logo
7:25 pm - 8:40 am
RDM
-
MDW
11h 15m
2 stops
Delta Logo
2:00 pm - 10:47 pm
MDW
-
RDM
10h 47m
2 stops
$600Delta
Thu, Aug 27 - Mon, Aug 31
Delta Logo
5:55 am - 6:05 pm
RDM
-
MDW
10h 10m
2 stops
Delta Logo
2:00 pm - 10:47 pm
MDW
-
RDM
10h 47m
2 stops
$602Delta
Tue, Aug 18 - Sat, Aug 22

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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
May 23
RDM7:20 pmBend/Redmond
11h 23m
2 stops
MDW8:43 amChicago Midway
May 30
MDW9:22 amChicago Midway
11h 13m
2 stops
RDM6:35 pmBend/Redmond
$397
Delta
Jul 3
RDM5:20 amBend/Redmond
10h 58m
2 stops
MDW6:18 pmChicago Midway
Jul 8
MDW1:18 pmChicago Midway
12h 40m
2 stops
RDM11:58 pmBend/Redmond
$479
Delta
May 19
RDM7:20 pmBend/Redmond
11h 23m
2 stops
MDW8:43 amChicago Midway
May 23
MDW1:22 pmChicago Midway
10h 52m
2 stops
RDM10:14 pmBend/Redmond
$487

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 May 5, 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

Sat 5/23

7:20 pm-8:43 am

2 stops11h 23m

Chicago Midway

Sat 5/30

9:22 am-6:35 pm

2 stops11h 13m

$397

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Fri 7/3

5:20 am-6:18 pm

2 stops10h 58m

Chicago Midway

Wed 7/8

1:18 pm-11:58 pm

2 stops12h 40m

$479

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Tue 5/19

7:20 pm-8:43 am

2 stops11h 23m

Chicago Midway

Sat 5/23

1:22 pm-10:14 pm

2 stops10h 52m

$487

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Fri 7/3

7:25 pm-8:37 am

2 stops11h 12m

Chicago Midway

Wed 7/8

1:49 pm-11:58 pm

2 stops12h 09m

$537

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Wed 5/20

6:10 am-6:33 pm

2 stops10h 23m

Chicago Midway

Wed 5/27

1:22 pm-10:54 pm

2 stops11h 32m

$540

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Fri 7/3

5:20 am-6:18 pm

2 stops10h 58m

Chicago Midway

Wed 7/8

1:49 pm-11:58 pm

2 stops12h 09m

$579

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Fri 6/19

7:25 pm-8:37 am

2 stops11h 12m

Chicago Midway

Mon 6/22

6:00 am-10:58 pm

2 stops18h 58m

$586

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Sat 5/30

5:05 am-6:33 pm

2 stops11h 28m

Chicago Midway

Sun 5/31

1:59 pm-11:44 pm

2 stops11h 45m

$598

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Thu 8/27

7:25 pm-8:40 am

2 stops11h 15m

Chicago Midway

Mon 8/31

2:00 pm-10:47 pm

2 stops10h 47m

$600
Quickest round-trip

RedmondChicago

RDM - MDW

RDMMDW

Bend/Redmond

Tue 8/18

5:55 am-6:05 pm

2 stops10h 10m

Chicago Midway

Sat 8/22

2:00 pm-10:47 pm

2 stops10h 47m

$602

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

9h 47m

Direct flights

None
The fastest flight from Redmond to Chicago Midway Airport takes 9h 47m
There are no direct flights from Redmond to Chicago Midway Airport. There are no popular flight routes from Redmond to Chicago Midway Airport.
Search flight deals

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 9h 47m.

  • 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
Saint Joseph
Benton Harbor
Portage
Lansing
Valparaiso
Munster
Schererville
Crown Point
Monticello
Chesterton
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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