Find Cheap Flights from Los Angeles to Chicago Midway (LAX - MDW)

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Good to Know

Low Season:
February
Best time to beat the crowds
3%
expected price decrease
High Season:
June
Most popular time to fly
11%
expected price increase
Average Price:
$366
(avg. price over the last 2 weeks)
Good Deal:
$264
or less (round trip)

When to Book Flights from Los Angeles to Chicago Midway

Average price per month
Flight prices as travel date approaches
-1 day
-2 days

Top tips for Finding a Cheap Flight

Looking for a cheap flight? 25% of our users found flights on this route for $263 or less.
The cheapest flight from Los Angeles to Chicago Midway was found 79 days before departure, on average.
Book at least 2 weeks before departure in order to get a below-average price.
High season is considered to be May, June and July. The cheapest month to fly is February.
Morning departure is around 2% cheaper than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

FAQs for Booking Los Angeles to Chicago Midway Flights

How long does a flight from Los Angeles to Chicago Midway take?
An average nonstop flight takes 6h 01m, covering a distance of 1747 miles.
How many flights are there between Los Angeles and Chicago Midway?
There are 47 (nonstop) flights between Los Angeles and Chicago Midway per week, averaging 6 per day.
Which airlines provide the cheapest flights from Los Angeles to Chicago Midway?
In the past 3 days, the cheapest round-trip tickets were found on Delta ($254)
Do I need a passport to fly between Los Angeles and Chicago Midway?
No.
Which airlines fly most frequently between Los Angeles and Chicago Midway?
Southwest (6 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Los Angeles to Chicago Midway?
For Los Angeles to Chicago Midway, Tuesday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Chicago Midway back to Los Angeles, the best deals are generally found on Saturday, with Sunday being the most expensive.

Book cheap flights from Los Angeles to Chicago Midway (round-trip)

Airports
Origin
Los Angeles
$254
only
$254
Destination
Chicago
$254
only
$254
Tue, Jan 16
LAX
MDW
6h 01m
Tue, Jan 23
MDW
LAX
9h 19m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SDQ
ATL
Excellent 8.0

Wasted my time on security and lost my flight

ORF
BOS
Excellent 10.0

Flight attendant Gillian Awesome. Crew was fun and made my kids first flight great.

SLC
MEX
Good 7.0

They hade entertainment

No food

DTW
PHL
Excellent 8.0

Made it out of Detroit that same day! Friendly flight attendants!

Flight was delayed. And then cancelled. We were booked into a later flight 8 hours later that was also delayed again due to weather but we did make it out of Detroit that night. Other people were not as lucky.

MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

Wed, Jan 17
LAX
MDW
7h 04m
Wed, Jan 31
MDW
LAX
7h 01m
Trip: 15 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SDQ
ATL
Excellent 8.0

Wasted my time on security and lost my flight

MSP
DSM
Good 6.0

The plane went where it was supposed to go.

MSP
LAS
Good 6.6

comfortable seats

delay delay delay

ORD
MSP
Okay 4.0

I needed to run real fast to the connection flight and gladly got there on time.

MSY
JFK
Excellent 10.0

Love the new in-cabin wi-fi, USB charging station, and menu of in-flight entertainment and resources on the individual flatscreens.

Thu, Jan 18
LAX
MDW
6h 47m
Sat, Feb 10
MDW
LAX
6h 36m
Trip: 24 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

DTW
PHL
Excellent 8.0

Made it out of Detroit that same day! Friendly flight attendants!

Flight was delayed. And then cancelled. We were booked into a later flight 8 hours later that was also delayed again due to weather but we did make it out of Detroit that night. Other people were not as lucky.

MSP
LAS
Good 6.6

comfortable seats

delay delay delay

CUN
MSP
Okay 4.3

The Cancun airport provides a terrible experience for transferring between flights, especially if you need to change from the international terminal to a domestic terminal or vice-versa. There is no way to get between terminals inside security and the free shuttle is slow and overcrowded. Meanwhile, one is forced to run a gauntlet of taxi and shuttle drivers trying to get you to pay them exorbitant fees to drive you to your terminal. Once you finally arrive you discover that there is no dedicated baggage recheck for an international arrival. Just don't buy a ticket that transfers in CUN.

YUL
MSP
Good 6.0

We got on the plane and it went to where it was supposed to go.

Fri, Jan 19
LAX
MDW
9h 25m
Tue, Jan 23
MDW
LAX
8h 32m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSY
JFK
Excellent 10.0

Love the new in-cabin wi-fi, USB charging station, and menu of in-flight entertainment and resources on the individual flatscreens.

DTW
PHL
Excellent 8.0

Made it out of Detroit that same day! Friendly flight attendants!

Flight was delayed. And then cancelled. We were booked into a later flight 8 hours later that was also delayed again due to weather but we did make it out of Detroit that night. Other people were not as lucky.

SLC
MEX
Good 7.0

They hade entertainment

No food

YUL
MSP
Good 6.0

We got on the plane and it went to where it was supposed to go.

ORD
MSP
Okay 4.0

I needed to run real fast to the connection flight and gladly got there on time.

Sat, Jan 20
LAX
MDW
8h 54m
Mon, Jan 29
MDW
LAX
6h 30m
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SDQ
ATL
Excellent 8.0

Wasted my time on security and lost my flight

CUN
MSP
Okay 4.3

The Cancun airport provides a terrible experience for transferring between flights, especially if you need to change from the international terminal to a domestic terminal or vice-versa. There is no way to get between terminals inside security and the free shuttle is slow and overcrowded. Meanwhile, one is forced to run a gauntlet of taxi and shuttle drivers trying to get you to pay them exorbitant fees to drive you to your terminal. Once you finally arrive you discover that there is no dedicated baggage recheck for an international arrival. Just don't buy a ticket that transfers in CUN.

SLC
MEX
Good 7.0

They hade entertainment

No food

MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

MSP
LAS
Good 6.6

comfortable seats

delay delay delay

Mon, Jan 22
LAX
MDW
7h 31m
Thu, Jan 25
MDW
LAX
7h 24m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ORD
MSP
Okay 4.0

I needed to run real fast to the connection flight and gladly got there on time.

DTW
PHL
Excellent 8.0

Made it out of Detroit that same day! Friendly flight attendants!

Flight was delayed. And then cancelled. We were booked into a later flight 8 hours later that was also delayed again due to weather but we did make it out of Detroit that night. Other people were not as lucky.

MSY
JFK
Excellent 10.0

Love the new in-cabin wi-fi, USB charging station, and menu of in-flight entertainment and resources on the individual flatscreens.

SLC
MEX
Good 7.0

They hade entertainment

No food

MSP
LAS
Good 6.6

comfortable seats

delay delay delay

Tue, Jan 23
LAX
MDW
6h 47m
Fri, Jan 26
MDW
LAX
7h 35m
Trip: 4 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

ORD
MSP
Okay 4.0

I needed to run real fast to the connection flight and gladly got there on time.

ORF
BOS
Excellent 10.0

Flight attendant Gillian Awesome. Crew was fun and made my kids first flight great.

SDQ
ATL
Excellent 8.0

Wasted my time on security and lost my flight

MSY
JFK
Excellent 10.0

Love the new in-cabin wi-fi, USB charging station, and menu of in-flight entertainment and resources on the individual flatscreens.

Wed, Jan 24
LAX
MDW
6h 41m
Wed, Jan 31
MDW
LAX
6h 49m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DTW
PHL
Excellent 8.0

Made it out of Detroit that same day! Friendly flight attendants!

Flight was delayed. And then cancelled. We were booked into a later flight 8 hours later that was also delayed again due to weather but we did make it out of Detroit that night. Other people were not as lucky.

ORF
BOS
Excellent 10.0

Flight attendant Gillian Awesome. Crew was fun and made my kids first flight great.

CUN
MSP
Okay 4.3

The Cancun airport provides a terrible experience for transferring between flights, especially if you need to change from the international terminal to a domestic terminal or vice-versa. There is no way to get between terminals inside security and the free shuttle is slow and overcrowded. Meanwhile, one is forced to run a gauntlet of taxi and shuttle drivers trying to get you to pay them exorbitant fees to drive you to your terminal. Once you finally arrive you discover that there is no dedicated baggage recheck for an international arrival. Just don't buy a ticket that transfers in CUN.

CMH
DTW
Excellent 8.6

Easy to board.

Delayed due to weather.

SLC
MEX
Good 7.0

They hade entertainment

No food

Thu, Jan 25
LAX
MDW
9h 25m
Sat, Feb 3
MDW
LAX
9h 30m
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SLC
MEX
Good 7.0

They hade entertainment

No food

MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

YUL
MSP
Good 6.0

We got on the plane and it went to where it was supposed to go.

ORF
BOS
Excellent 10.0

Flight attendant Gillian Awesome. Crew was fun and made my kids first flight great.

SDQ
ATL
Excellent 8.0

Wasted my time on security and lost my flight

Sat, Jan 27
LAX
MDW
9h 27m
Wed, Jan 31
MDW
LAX
9h 19m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SLC
MEX
Good 7.0

They hade entertainment

No food

DTW
PHL
Excellent 8.0

Made it out of Detroit that same day! Friendly flight attendants!

Flight was delayed. And then cancelled. We were booked into a later flight 8 hours later that was also delayed again due to weather but we did make it out of Detroit that night. Other people were not as lucky.

MSP
DSM
Good 6.0

The plane went where it was supposed to go.

MSY
JFK
Excellent 10.0

Love the new in-cabin wi-fi, USB charging station, and menu of in-flight entertainment and resources on the individual flatscreens.

SDQ
ATL
Excellent 8.0

Wasted my time on security and lost my flight

Mon, Jan 29
LAX
MDW
7h 31m
Mon, Feb 5
MDW
LAX
9h 33m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ORD
MSP
Okay 4.0

I needed to run real fast to the connection flight and gladly got there on time.

MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

MSY
JFK
Excellent 10.0

Love the new in-cabin wi-fi, USB charging station, and menu of in-flight entertainment and resources on the individual flatscreens.

SLC
MEX
Good 7.0

They hade entertainment

No food

YUL
MSP
Good 6.0

We got on the plane and it went to where it was supposed to go.

Tue, Jan 30
LAX
MDW
8h 55m
Sat, Feb 3
MDW
LAX
9h 30m
Trip: 5 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
YUL
MSP
Good 6.0

We got on the plane and it went to where it was supposed to go.

MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

MSY
JFK
Excellent 10.0

Love the new in-cabin wi-fi, USB charging station, and menu of in-flight entertainment and resources on the individual flatscreens.

DTW
PHL
Excellent 8.0

Made it out of Detroit that same day! Friendly flight attendants!

Flight was delayed. And then cancelled. We were booked into a later flight 8 hours later that was also delayed again due to weather but we did make it out of Detroit that night. Other people were not as lucky.

ORF
BOS
Excellent 10.0

Flight attendant Gillian Awesome. Crew was fun and made my kids first flight great.

Wed, Jan 31
LAX
MDW
6h 27m
Mon, Feb 12
MDW
LAX
8h 48m
Trip: 13 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
YUL
MSP
Good 6.0

We got on the plane and it went to where it was supposed to go.

CUN
MSP
Okay 4.3

The Cancun airport provides a terrible experience for transferring between flights, especially if you need to change from the international terminal to a domestic terminal or vice-versa. There is no way to get between terminals inside security and the free shuttle is slow and overcrowded. Meanwhile, one is forced to run a gauntlet of taxi and shuttle drivers trying to get you to pay them exorbitant fees to drive you to your terminal. Once you finally arrive you discover that there is no dedicated baggage recheck for an international arrival. Just don't buy a ticket that transfers in CUN.

MSY
JFK
Excellent 10.0

Love the new in-cabin wi-fi, USB charging station, and menu of in-flight entertainment and resources on the individual flatscreens.

MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

MSP
LAS
Good 6.6

comfortable seats

delay delay delay

Thu, Feb 1
LAX
MDW
7h 38m
Fri, Feb 9
MDW
LAX
7h 35m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
SDQ
ATL
Excellent 8.0

Wasted my time on security and lost my flight

SLC
MEX
Good 7.0

They hade entertainment

No food

ORD
MSP
Okay 4.0

I needed to run real fast to the connection flight and gladly got there on time.

MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

MSY
JFK
Excellent 10.0

Love the new in-cabin wi-fi, USB charging station, and menu of in-flight entertainment and resources on the individual flatscreens.

Fri, Feb 2
LAX
MDW
7h 31m
Sat, Feb 10
MDW
LAX
6h 36m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
ORF
BOS
Excellent 10.0

Flight attendant Gillian Awesome. Crew was fun and made my kids first flight great.

MSP
DSM
Good 6.0

The plane went where it was supposed to go.

CMH
DTW
Excellent 8.6

Easy to board.

Delayed due to weather.

SDQ
ATL
Excellent 8.0

Wasted my time on security and lost my flight

MSP
LAS
Good 6.6

comfortable seats

delay delay delay

Sat, Feb 3
LAX
MDW
6h 10m
Sat, Feb 10
MDW
LAX
7h 35m
Trip: 8 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
DTW
PHL
Excellent 8.0

Made it out of Detroit that same day! Friendly flight attendants!

Flight was delayed. And then cancelled. We were booked into a later flight 8 hours later that was also delayed again due to weather but we did make it out of Detroit that night. Other people were not as lucky.

MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

SLC
MEX
Good 7.0

They hade entertainment

No food

YUL
MSP
Good 6.0

We got on the plane and it went to where it was supposed to go.

ORF
BOS
Excellent 10.0

Flight attendant Gillian Awesome. Crew was fun and made my kids first flight great.

Sun, Feb 4
LAX
MDW
6h 35m
Tue, Feb 13
MDW
LAX
7h 24m
Trip: 10 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSP
DSM
Good 6.0

The plane went where it was supposed to go.

MSY
JFK
Excellent 10.0

Love the new in-cabin wi-fi, USB charging station, and menu of in-flight entertainment and resources on the individual flatscreens.

MSP
LAS
Good 6.6

comfortable seats

delay delay delay

CUN
MSP
Okay 4.3

The Cancun airport provides a terrible experience for transferring between flights, especially if you need to change from the international terminal to a domestic terminal or vice-versa. There is no way to get between terminals inside security and the free shuttle is slow and overcrowded. Meanwhile, one is forced to run a gauntlet of taxi and shuttle drivers trying to get you to pay them exorbitant fees to drive you to your terminal. Once you finally arrive you discover that there is no dedicated baggage recheck for an international arrival. Just don't buy a ticket that transfers in CUN.

ORD
MSP
Okay 4.0

I needed to run real fast to the connection flight and gladly got there on time.

Mon, Feb 5
LAX
MDW
7h 31m
Tue, Feb 13
MDW
LAX
7h 35m
Trip: 9 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSP
LAS
Good 6.6

comfortable seats

delay delay delay

MSP
DSM
Good 6.0

The plane went where it was supposed to go.

CUN
MSP
Okay 4.3

The Cancun airport provides a terrible experience for transferring between flights, especially if you need to change from the international terminal to a domestic terminal or vice-versa. There is no way to get between terminals inside security and the free shuttle is slow and overcrowded. Meanwhile, one is forced to run a gauntlet of taxi and shuttle drivers trying to get you to pay them exorbitant fees to drive you to your terminal. Once you finally arrive you discover that there is no dedicated baggage recheck for an international arrival. Just don't buy a ticket that transfers in CUN.

ORF
BOS
Excellent 10.0

Flight attendant Gillian Awesome. Crew was fun and made my kids first flight great.

ORD
MSP
Okay 4.0

I needed to run real fast to the connection flight and gladly got there on time.

Tue, Feb 6
LAX
MDW
7h 31m
Thu, Feb 22
MDW
LAX
8h 03m
Trip: 17 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
CMH
DTW
Excellent 8.6

Easy to board.

Delayed due to weather.

MSP
DSM
Good 6.0

The plane went where it was supposed to go.

CUN
MSP
Okay 4.3

The Cancun airport provides a terrible experience for transferring between flights, especially if you need to change from the international terminal to a domestic terminal or vice-versa. There is no way to get between terminals inside security and the free shuttle is slow and overcrowded. Meanwhile, one is forced to run a gauntlet of taxi and shuttle drivers trying to get you to pay them exorbitant fees to drive you to your terminal. Once you finally arrive you discover that there is no dedicated baggage recheck for an international arrival. Just don't buy a ticket that transfers in CUN.

MSY
JFK
Excellent 10.0

Love the new in-cabin wi-fi, USB charging station, and menu of in-flight entertainment and resources on the individual flatscreens.

DTW
PHL
Excellent 8.0

Made it out of Detroit that same day! Friendly flight attendants!

Flight was delayed. And then cancelled. We were booked into a later flight 8 hours later that was also delayed again due to weather but we did make it out of Detroit that night. Other people were not as lucky.

Wed, Feb 7
LAX
MDW
6h 27m
Sat, Feb 17
MDW
LAX
9h 16m
Trip: 11 days
7.8GoodShow reviews
Overall 7.8 Good
Based on 15076 reviews
Overall
8.0
Boarding
8.1
Comfort
7.7
Crew
8.4
Entertainment
7.5
Food
7.3
MSY
JFK
Excellent 10.0

Love the new in-cabin wi-fi, USB charging station, and menu of in-flight entertainment and resources on the individual flatscreens.

SDQ
ATL
Excellent 8.0

Wasted my time on security and lost my flight

SLC
MEX
Good 7.0

They hade entertainment

No food

MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

MSP
LAS
Good 6.6

comfortable seats

delay delay delay

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Los Angeles to Chicago Midway Flight Information

Flights Arrive in Chicago Midway
Flights Depart from Los Angeles
Flight Price $254
Distance 1747 miles
Airlines Delta