Find Cheap Flights from Chicago Midway to Dallas Love Field (MDW - DAL)

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Fri 12/15
Fri 12/22
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Looking for a cheap flight? 25% of our users found flights on this route for $203 or less.

FAQs for Booking Chicago Midway to Dallas Love Field Flights

How long does a flight from Chicago Midway to Dallas Love Field take?
An average nonstop flight takes 2h 20m, covering a distance of 793 miles.
How many flights are there between Chicago Midway and Dallas Love Field?
There are 134 (nonstop) flights between Chicago Midway and Dallas Love Field per week, averaging 19 per day.
Which airlines provide the cheapest flights from Chicago Midway to Dallas Love Field?
In the past 3 days, the cheapest round-trip tickets were found on Delta ($197) and Southwest ($230)
Do I need a passport to fly between Chicago Midway and Dallas Love Field?
No.
Which airlines fly most frequently between Chicago Midway and Dallas Love Field?
Southwest (19 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Chicago Midway to Dallas Love Field?
For Chicago Midway to Dallas Love Field, Tuesday is the cheapest day to fly on average and Thursday is the most expensive. Flying from Dallas Love Field back to Chicago Midway, the best deals are generally found on Wednesday, with Friday being the most expensive.

Book cheap flights from Chicago Midway to Dallas Love Field (round-trip)

Airports
Origin
Chicago
$197
only
$197
Destination
Dallas
$197
only
$197
Tue, Jan 23
MDW
DAL
6h 35m
Fri, Jan 26
DAL
MDW
4h 39m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SLC
SJC
Excellent 9.6

As always, the crew and amenities were first rate.

We were initially told that our flight would arrive early. Then we sat on the tarmac for a half hour before anyone could be bothered to tell us we were waiting for the plane to be de-iced.

SLC
SNA
Excellent 8.0

Comfortable seats in coach Good snacks Friendly crew

Nothing

MFR
SLC
Okay 4.6

Not sure who thought every passenger is 5'6 but for the rest of us, the seat pitch is ridiculously close. Like knees to the seat in front close. I'm 5'10 and I was very uncomfortable the entire flight.

See above

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

MSP
YXE
Excellent 9.3

I was traveling for medical reasons and the Delta crew took great care of me, made sure I was at my connecting gate on time, and even put me in a better seat on the plane. Not sure if that was a coincidental upgrade, or intentional, but it was perfect.

Thu, Feb 15
MDW
DAL
2h 20m
Mon, Feb 19
DAL
MDW
2h 10m
Trip: 5 days
8.8ExcellentShow reviews
Overall 8.8 Excellent
Based on 6 reviews
Boarding
8.8
Comfort
8.5
Crew
9.0
Entertainment
8.0
Food
7.9
SAT
MDW
Excellent 9.6

Southwest is now my favorite airline. They have the best crew ever and they got the process of boarding downpack.

SFO
LAX
Excellent 10.0

great staff! Great flight!!

DAL
MSY
Excellent 10.0

Great

HOU
CHS
Excellent 8.6

SWA is my favorite airline!

SAT
MCO
Excellent 10.0

Great service

Tue, Feb 20
MDW
DAL
5h 53m
Wed, Feb 28
DAL
MDW
4h 41m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

JFK
SFO
Excellent 10.0

Seats were comfortable ... enough. Boarding process, once underway allowed me to get overhead bin and stash my other luggage in the seat below me. Flight wasn't overly booked (85-95%) so there appeared to be room for others to stretch out. Now about that crying kid...

Ugh. Weather delays. The flight was scheduled to board about 7P but it arrived late and they had to not only unload the self-loading cargo, but clean up afterwards. Would be nice to get a better estimate as to how long it would take to board so that I could hang out in the lounge. In addition, departure from JFK was delayed as well, either we missed the IFR window or got stuck behind some traffic and I fell asleep on the plane only to wake up what seemed an hour later just getting ready to hit V1. No upgrade.

IND
DTW
Okay 4.0

No wifi couldn’t do any work

Was looking forward to completing some work but the wifi never came on.

SEA
LAX
Okay 4.0

Nothing, they didn’t care about you or to help, the llady was so rude and unfriendly, this situation ruin my whole trip

I call in advance to paid the fees for baggage, I call Aeromexico because was the main airline for the fly, but Delta at Seattle made me paid again the fees for baggage’s even by phone they said that I didn’t need to paid. BE AWARE AND CAREFUL BECAUSE THE LADIES IN THE FRONT DESK didn’t even look the paperwork that you have in hand, they only want to charge you saying that your payment thru Aeromexico didn’t help you in the 1st fly. How this can happen when Delta and Aeromexico are two subsidiary one of another ?

MFR
SLC
Okay 4.6

Not sure who thought every passenger is 5'6 but for the rest of us, the seat pitch is ridiculously close. Like knees to the seat in front close. I'm 5'10 and I was very uncomfortable the entire flight.

See above

Sat, Dec 16
MDW
DAL
6h 04m
Mon, Dec 18
DAL
MDW
5h 29m
Trip: 3 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SLC
SJC
Excellent 9.6

As always, the crew and amenities were first rate.

We were initially told that our flight would arrive early. Then we sat on the tarmac for a half hour before anyone could be bothered to tell us we were waiting for the plane to be de-iced.

JFK
SFO
Excellent 10.0

Seats were comfortable ... enough. Boarding process, once underway allowed me to get overhead bin and stash my other luggage in the seat below me. Flight wasn't overly booked (85-95%) so there appeared to be room for others to stretch out. Now about that crying kid...

Ugh. Weather delays. The flight was scheduled to board about 7P but it arrived late and they had to not only unload the self-loading cargo, but clean up afterwards. Would be nice to get a better estimate as to how long it would take to board so that I could hang out in the lounge. In addition, departure from JFK was delayed as well, either we missed the IFR window or got stuck behind some traffic and I fell asleep on the plane only to wake up what seemed an hour later just getting ready to hit V1. No upgrade.

ATL
ABE
Okay 4.0

Long wait for de-Icing. Got on and off the plane 3 times. First wait was 1 hour, but plane aborted takeoff. Second plane waited at gate with all aboard for 2-1/2 hours and never got slot and de-planed. Third plane waited 1-1/2 hours for de-Icing and finally we were headed home. Arrived 8.5 hours after schedule.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

MFR
SLC
Okay 4.6

Not sure who thought every passenger is 5'6 but for the rest of us, the seat pitch is ridiculously close. Like knees to the seat in front close. I'm 5'10 and I was very uncomfortable the entire flight.

See above

Wed, Mar 28
MDW
DAL
2h 20m
Sun, Apr 1
DAL
MDW
2h 10m
Trip: 5 days
8.8ExcellentShow reviews
Overall 8.8 Excellent
Based on 6 reviews
Boarding
8.8
Comfort
8.5
Crew
9.0
Entertainment
8.0
Food
7.9
LAX
MCI
Good 7.0

Crew is always very helpful especially with my kids

Wi-Fi didn't work, family boarding is after all the As board which is so wrong. Priority boarding should be for families with kids under 6

HOU
CHS
Excellent 8.6

SWA is my favorite airline!

MDW
DTW
Excellent 9.6

Southwest is now my favorite airline. They have the best crew ever and they got the process of boarding downpack.

SAT
MCO
Excellent 10.0

Great service

MDW
DAL
Excellent 10.0

Free bags, free change, great and friendly staff

Sat, Jan 6
MDW
DAL
6h 34m
Sat, Jan 13
DAL
MDW
6h 15m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
IND
DTW
Okay 4.0

No wifi couldn’t do any work

Was looking forward to completing some work but the wifi never came on.

SLC
SJC
Excellent 9.6

As always, the crew and amenities were first rate.

We were initially told that our flight would arrive early. Then we sat on the tarmac for a half hour before anyone could be bothered to tell us we were waiting for the plane to be de-iced.

SLC
SNA
Excellent 8.0

Comfortable seats in coach Good snacks Friendly crew

Nothing

LGA
YUL
Excellent 8.0

it was easy to navigate .

JFK
SFO
Excellent 10.0

Seats were comfortable ... enough. Boarding process, once underway allowed me to get overhead bin and stash my other luggage in the seat below me. Flight wasn't overly booked (85-95%) so there appeared to be room for others to stretch out. Now about that crying kid...

Ugh. Weather delays. The flight was scheduled to board about 7P but it arrived late and they had to not only unload the self-loading cargo, but clean up afterwards. Would be nice to get a better estimate as to how long it would take to board so that I could hang out in the lounge. In addition, departure from JFK was delayed as well, either we missed the IFR window or got stuck behind some traffic and I fell asleep on the plane only to wake up what seemed an hour later just getting ready to hit V1. No upgrade.

Thu, May 31
MDW
DAL
4h 52m
Wed, Jun 13
DAL
MDW
4h 46m
Trip: 14 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSP
YXE
Excellent 9.3

I was traveling for medical reasons and the Delta crew took great care of me, made sure I was at my connecting gate on time, and even put me in a better seat on the plane. Not sure if that was a coincidental upgrade, or intentional, but it was perfect.

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

LGA
YUL
Excellent 8.0

it was easy to navigate .

MFR
SLC
Okay 4.6

Not sure who thought every passenger is 5'6 but for the rest of us, the seat pitch is ridiculously close. Like knees to the seat in front close. I'm 5'10 and I was very uncomfortable the entire flight.

See above

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

Sat, Jun 2
MDW
DAL
4h 52m
Wed, Jun 13
DAL
MDW
4h 46m
Trip: 12 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

MSP
YXE
Excellent 9.3

I was traveling for medical reasons and the Delta crew took great care of me, made sure I was at my connecting gate on time, and even put me in a better seat on the plane. Not sure if that was a coincidental upgrade, or intentional, but it was perfect.

IND
DTW
Okay 4.0

No wifi couldn’t do any work

Was looking forward to completing some work but the wifi never came on.

SEA
LAX
Okay 4.0

Nothing, they didn’t care about you or to help, the llady was so rude and unfriendly, this situation ruin my whole trip

I call in advance to paid the fees for baggage, I call Aeromexico because was the main airline for the fly, but Delta at Seattle made me paid again the fees for baggage’s even by phone they said that I didn’t need to paid. BE AWARE AND CAREFUL BECAUSE THE LADIES IN THE FRONT DESK didn’t even look the paperwork that you have in hand, they only want to charge you saying that your payment thru Aeromexico didn’t help you in the 1st fly. How this can happen when Delta and Aeromexico are two subsidiary one of another ?

LGA
YUL
Excellent 8.0

it was easy to navigate .

Fri, Dec 22
MDW
DAL
5h 01m
Mon, Dec 25
DAL
MDW
7h 50m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SLC
SNA
Excellent 8.0

Comfortable seats in coach Good snacks Friendly crew

Nothing

SEA
LAX
Okay 5.3

Mu seat!

My baggage took for to long to arrive

LGA
YUL
Excellent 8.0

it was easy to navigate .

JFK
YYZ
Excellent 10.0

The staff is very friendly. Most pleasant airline I've flown with.

IND
DTW
Okay 4.0

No wifi couldn’t do any work

Was looking forward to completing some work but the wifi never came on.

Thu, May 17
MDW
DAL
4h 52m
Sun, May 20
DAL
MDW
5h 00m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 14207 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
LGA
YUL
Excellent 8.0

it was easy to navigate .

SEA
LAX
Okay 4.0

Nothing, they didn’t care about you or to help, the llady was so rude and unfriendly, this situation ruin my whole trip

I call in advance to paid the fees for baggage, I call Aeromexico because was the main airline for the fly, but Delta at Seattle made me paid again the fees for baggage’s even by phone they said that I didn’t need to paid. BE AWARE AND CAREFUL BECAUSE THE LADIES IN THE FRONT DESK didn’t even look the paperwork that you have in hand, they only want to charge you saying that your payment thru Aeromexico didn’t help you in the 1st fly. How this can happen when Delta and Aeromexico are two subsidiary one of another ?

SLC
SJC
Excellent 9.6

As always, the crew and amenities were first rate.

We were initially told that our flight would arrive early. Then we sat on the tarmac for a half hour before anyone could be bothered to tell us we were waiting for the plane to be de-iced.

IND
DTW
Okay 4.0

No wifi couldn’t do any work

Was looking forward to completing some work but the wifi never came on.

JFK
SFO
Excellent 10.0

Seats were comfortable ... enough. Boarding process, once underway allowed me to get overhead bin and stash my other luggage in the seat below me. Flight wasn't overly booked (85-95%) so there appeared to be room for others to stretch out. Now about that crying kid...

Ugh. Weather delays. The flight was scheduled to board about 7P but it arrived late and they had to not only unload the self-loading cargo, but clean up afterwards. Would be nice to get a better estimate as to how long it would take to board so that I could hang out in the lounge. In addition, departure from JFK was delayed as well, either we missed the IFR window or got stuck behind some traffic and I fell asleep on the plane only to wake up what seemed an hour later just getting ready to hit V1. No upgrade.

*
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