Find Cheap Flights from Bend/Redmond to Chicago Midway (RDM - MDW)

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Looking for a cheap flight? 25% of our users found flights on this route for $443 or less.

FAQs for Booking Bend/Redmond to Chicago Midway Flights

How long does a flight from Bend/Redmond to Chicago Midway take?
An average nonstop flight takes 8h 39m, covering a distance of 1684 miles.
Which airlines provide the cheapest flights from Bend/Redmond to Chicago Midway?
In the past 3 days, the cheapest round-trip tickets were found on Delta ($319)
Do I need a passport to fly between Bend/Redmond and Chicago Midway?
No.
What’s the cheapest day of the week to fly Bend/Redmond to Chicago Midway?
For Bend/Redmond to Chicago Midway, Tuesday is the cheapest day to fly on average and Monday is the most expensive. Flying from Chicago Midway back to Bend/Redmond, the best deals are generally found on Wednesday, with Friday being the most expensive.

Book cheap flights from Bend/Redmond to Chicago Midway (round-trip)

Airports
Origin
Bend
$319
only
$319
Destination
Chicago
$319
only
$319
Tue, Apr 10
RDM
MDW
8h 39m
Wed, Apr 11
MDW
RDM
11h 29m
Trip: 2 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

Wed, Apr 11
RDM
MDW
8h 39m
Wed, Apr 18
MDW
RDM
11h 56m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

Tue, Apr 10
RDM
MDW
8h 39m
Mon, Apr 16
MDW
RDM
11h 29m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

JFK
CDG
Excellent 10.0

The food and the service

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

Wed, Apr 11
RDM
MDW
8h 39m
Sat, Apr 21
MDW
RDM
12h 04m
Trip: 11 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

JFK
CDG
Excellent 10.0

The food and the service

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

Tue, Apr 17
RDM
MDW
8h 39m
Sat, Apr 21
MDW
RDM
11h 40m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

Wed, Apr 18
RDM
MDW
8h 39m
Sat, Apr 21
MDW
RDM
12h 04m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

JFK
CDG
Excellent 10.0

The food and the service

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

Tue, Apr 10
RDM
MDW
8h 39m
Thu, Apr 12
MDW
RDM
11h 56m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

JFK
CDG
Excellent 10.0

The food and the service

FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

Wed, Apr 11
RDM
MDW
8h 39m
Fri, Apr 20
MDW
RDM
11h 56m
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

SLC
YYZ
Excellent 9.6

Z

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

Thu, Apr 12
RDM
MDW
8h 39m
Tue, Apr 17
MDW
RDM
11h 29m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

Fri, Apr 13
RDM
MDW
8h 39m
Wed, Apr 18
MDW
RDM
11h 56m
Trip: 6 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

JFK
CDG
Excellent 10.0

The food and the service

Wed, Apr 11
RDM
MDW
8h 39m
Thu, Apr 19
MDW
RDM
11h 56m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

JFK
CDG
Excellent 10.0

The food and the service

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

SLC
YYZ
Excellent 9.6

Z

Thu, Apr 12
RDM
MDW
8h 39m
Sat, Apr 21
MDW
RDM
11h 40m
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

SLC
YYZ
Excellent 9.6

Z

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

Fri, Apr 13
RDM
MDW
8h 39m
Mon, Apr 16
MDW
RDM
11h 56m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

PIT
ATL
Excellent 10.0

I have always known of airlines to offer preboarding to those military members in uniform or on official orders. Delta took it one step further and allows prior service members to board also.

SLC
YYZ
Excellent 9.6

Z

Thu, Apr 12
RDM
MDW
8h 39m
Fri, Apr 20
MDW
RDM
11h 56m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

Fri, Apr 13
RDM
MDW
8h 39m
Thu, Apr 19
MDW
RDM
11h 56m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

Tue, Apr 10
RDM
MDW
8h 39m
Sat, Apr 14
MDW
RDM
10h 19m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

JFK
CDG
Excellent 10.0

The food and the service

Wed, Apr 11
RDM
MDW
8h 39m
Sat, Apr 14
MDW
RDM
10h 19m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
FLL
BOS
Good 6.3

Food and nice crew

No tvs and bad WiFi

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

FLL
ATL
Excellent 8.0

Departure was right on time and we actually arrived 15 minutes early.

The inflight monitor worked but none of the data (GPS altitude or speed) was working.

Mon, Mar 5
RDM
MDW
8h 43m
Mon, Mar 12
MDW
RDM
11h 56m
Trip: 7 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

LAX
MCO
Excellent 10.0

I am used to flying Frontier because of cost but recently traveled Delta and boy did I feel completely spoiled! Not only did my other half get our bags for free due to his status with Delta but the amenities they offer and the comfort of the economy seats compared to other airlines is a major difference. As a chronic pain patient, if I can find a Delta flight for a little more, I will be booking with them for sure! Highly recommend them!

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

LAX
MSP
Excellent 9.0

Had to sit in the middle row and I wasn’t given the option to get an aisle sit during check in.

No flexibility for seats

JFK
CDG
Excellent 10.0

The food and the service

Mon, Apr 9
RDM
MDW
8h 39m
Wed, Apr 18
MDW
RDM
11h 56m
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

SLC
YYZ
Excellent 9.6

Z

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

ATL
PIT
Excellent 9.0

Pilots and crew did an amazing job during unstable air coming into Pittsburgh. Great job.

MSP
CLT
Excellent 10.0

It was great because I was able to get an aisle seat.

Like it all

Tue, Apr 10
RDM
MDW
8h 39m
Fri, Apr 13
MDW
RDM
9h 53m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 16166 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.5
Food
7.4
JFK
CDG
Excellent 10.0

The food and the service

MSP
CZM
Excellent 10.0

Everything went smoothly.

All was good.

SLC
YYZ
Excellent 8.0

was a difficult transition from delta to west jet in Toronto and we almost missed the flight

SLC
YYZ
Excellent 9.6

Z

JFK
MCO
Excellent 8.0

Entertainment system great. Individual choices include recent movies. On board staff very nice

We had issues with baggage. Delta was supposed to transfer 4 bags to Disney for Magic Express transportation. Only 3 went. Disney tried hard to fix problem, and even gave us something to ameliorate the situation. Delta took hard line, wasn't helpful and gave nothing. It took 2 days to find bag.

Bend/Redmond to Chicago Midway Flight Information

Flights Arrive in Chicago Midway
Flights Depart from Bend/Redmond
Flight Price $319
Distance 1684 miles
Airlines Delta
*
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The fares displayed include all taxes and fees for economy class travel and were found by the provider in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.