Find Cheap Flights from Chicago Midway to Jacksonville (MDW - JAX)

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Good to Know

Average Price:
$387
(avg. price over the last 2 weeks)
Good Deal:
$315
or less (round trip)

When to Book Flights from Chicago Midway to Jacksonville

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 $315 or less.
The cheapest flight from Chicago Midway to Jacksonville was found 76 days before departure, on average.
Book at least 2 weeks before departure in order to get a below-average price.
Morning departure is around 14% more expensive 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 Chicago Midway to Jacksonville Flights

How long does a flight from Chicago Midway to Jacksonville take?
An average nonstop flight takes 3h 37m, covering a distance of 850 miles.
How many flights are there between Chicago Midway and Jacksonville?
There are 9 (nonstop) flights between Chicago Midway and Jacksonville per week, averaging 1 per day.
Which airlines provide the cheapest flights from Chicago Midway to Jacksonville?
In the past 3 days, the cheapest round-trip tickets were found on Delta ($210)
Do I need a passport to fly between Chicago Midway and Jacksonville?
No.
Which airlines fly most frequently between Chicago Midway and Jacksonville?
Southwest (1 times daily) are the most frequent flyers on this route.
What’s the cheapest day of the week to fly Chicago Midway to Jacksonville?
For Chicago Midway to Jacksonville, Tuesday is the cheapest day to fly on average and Wednesday is the most expensive. Flying from Jacksonville back to Chicago Midway, the best deals are generally found on Thursday, with Saturday being the most expensive.

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

Airports
Origin
Chicago
$210
only
$210
Destination
Jacksonville
$210
only
$210
Tue, Feb 6
MDW
JAX
5h 15m
Mon, Feb 12
JAX
MDW
6h 54m
Trip: 7 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.

YUL
MSP
Good 6.0

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

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

Sat, Mar 3
MDW
JAX
6h 37m
Mon, Mar 5
JAX
MDW
4h 23m
Trip: 3 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.

SLC
MEX
Good 7.0

They hade entertainment

No food

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.

MSP
DSM
Good 6.0

The plane went where it was supposed to go.

Tue, Apr 17
MDW
JAX
4h 03m
Tue, Apr 24
JAX
MDW
4h 44m
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
MSP
DSM
Good 6.0

The plane went where it was supposed to go.

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.

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.

ORF
BOS
Excellent 10.0

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

Mon, Apr 30
MDW
JAX
4h 38m
Mon, May 7
JAX
MDW
4h 23m
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
MSP
DSM
Good 6.0

The plane went 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.

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.

SDQ
ATL
Excellent 8.0

Wasted my time on security and lost my flight

Wed, May 2
MDW
JAX
3h 37m
Wed, May 9
JAX
MDW
3h 54m
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
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

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.

MSP
DSM
Good 6.0

The plane went where it was supposed to go.

Tue, May 15
MDW
JAX
3h 46m
Tue, May 22
JAX
MDW
4h 37m
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
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.

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
DSM
Good 6.0

The plane went where it was supposed to go.

Wed, Jan 31
MDW
JAX
5h 15m
Sat, Feb 3
JAX
MDW
5h 28m
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
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
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.

YUL
MSP
Good 6.0

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

Wed, Feb 7
MDW
JAX
4h 41m
Fri, Feb 9
JAX
MDW
5h 29m
Trip: 3 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

SDQ
ATL
Excellent 8.0

Wasted my time on security and lost my flight

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.

Mon, Jul 9
MDW
JAX
6h 56m
Sat, Jul 14
JAX
MDW
5h 10m
Trip: 6 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

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.

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

Mon, Jun 25
MDW
JAX
4h 57m
Tue, Jun 26
JAX
MDW
4h 00m
Trip: 2 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.

ORD
MSP
Okay 4.0

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

CMH
DTW
Excellent 8.6

Easy to board.

Delayed due to weather.

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

Sun, Mar 11
MDW
JAX
5h 38m
Fri, Mar 16
JAX
MDW
4h 23m
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
SDQ
ATL
Excellent 8.0

Wasted my time on security and lost my flight

MSP
LAS
Good 6.6

comfortable seats

delay delay delay

YUL
MSP
Good 6.0

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

MSP
DSM
Good 6.0

The plane went where it was supposed to go.

MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

Fri, Mar 23
MDW
JAX
5h 38m
Thu, Mar 29
JAX
MDW
6h 19m
Trip: 7 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.

SDQ
ATL
Excellent 8.0

Wasted my time on security and lost my flight

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.

MSP
LAS
Good 6.6

comfortable seats

delay delay delay

Wed, Jan 17
MDW
JAX
5h 16m
Thu, Jan 18
JAX
MDW
4h 24m
Trip: 2 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
DSM
Good 6.0

The plane went where it was supposed to go.

MSP
SFO
Good 7.0

Delayed take off and waited for the bridgr

MSP
LAS
Good 6.6

comfortable seats

delay delay delay

SDQ
ATL
Excellent 8.0

Wasted my time on security and lost my flight

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*
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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.

Chicago Midway to Jacksonville Flight Information

Flights Arrive in Jacksonville
Flights Depart from Chicago Midway
Flight Price $210
Distance 850 miles
Airlines Delta