MDW - OAJ

Find Cheap Flights from Chicago Midway to Jacksonville

Round-trip
Economy
Chicago (MDW)
Jacksonville Albert J Ellis
Mon 9/16
Mon 9/23
Any month
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Chicago Midway to Jacksonville Flight Information

Flights Arrive in Jacksonville Albert J Ellis
Flights Depart from Chicago Midway
Flight Price $345
Distance 729 miles
Airlines Delta

FAQs for Booking Chicago Midway to Jacksonville Flights

How long does a flight from Chicago Midway to Jacksonville take?
There are no direct flights for this route listed on KAYAK, the shortest multi-flight duration is 4h 02m.
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 ($345)
Do I need a passport to fly between Chicago Midway and Jacksonville?
No.
What’s the cheapest day of the week to fly Chicago Midway to Jacksonville?
For Chicago Midway to Jacksonville, Saturday 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 Tuesday, with Friday being the most expensive.
How does KAYAK find such low flight prices?
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How can Hacker Fares save me money?
Hacker Fares allow you to combine one-way tickets on different airlines when it can save you money over a traditional round-trip ticket.
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Book cheap flights from Chicago Midway to Jacksonville (round-trip)

Airports
Origin
Chicago
$345
only
$345
Destination
Jacksonville
$345
only
$345
Sat, Sep 21
MDW
Chicago Midway
OAJ
Jacksonville Albert J Ellis
6h 34m
Thu, Sep 26
OAJ
Jacksonville Albert J Ellis
MDW
Chicago Midway
6h 15m
Trip: 6 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 26,222 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.5
SFO
SEA
Excellent 8.0

Pros: Smooth, efficient and timely.

Cons: Seats weren’t assigned until at the gate even though checked in 18 hours before. Bag drop was horrible. No self service. Was inline for about 45 minutes.

MIA
JFK
Excellent 10.0

Pros: I loved being upgraded to first class and the crew was so attentive.

Cons: Nothing, glad this was a better experience than the trip to Miami.

MSP
BOS
Okay 5.0

Cons: Flight attendant in First class was visibly frustrated and unfriendly. He was not helping with my simple request for a blanket. Also, the were no food service in first class.

ATL
MYR
Excellent 10.0

Pros: Awesome crew

Cons: More room

LHR
JFK
Excellent 8.0

Pros: Food was great. Movie selection was good.

Cons: When we booked our flight, we were not informed by KAYAK that we have to pay for our luggage! I t was very unpleasant surprise both ways.

Fri, Sep 6
MDW
Chicago Midway
OAJ
Jacksonville Albert J Ellis
4h 02m
Sat, Sep 14
OAJ
Jacksonville Albert J Ellis
MDW
Chicago Midway
6h 25m
Trip: 9 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 26,222 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.5
BOS
MCI
Excellent 8.0

Pros: The crew was polite and pleasant unlike the crew from KC to Boston.

Cons: Telling us to check bags before we get to our seat and find out there is no more room.

SLC
BNA
Excellent 9.6

Pros: Crew was great, seats were comfy and the entertainment options were good.

Cons: Flight was delayed but it happens.

MCO
LAX
Excellent 8.0

Pros: Gogo in flight entertainment and WiFi worked well

Cons: Collect the trash sooner. Hot food options.

SEA
YVR
Good 7.5

Pros: The crew were nice.

Cons: We could have used more legroom between the seats.

LGA
IAH
Excellent 8.3

Pros: There were a few hiccups with the overall flight process, but the crew was very friendly and informed everyone in a timely manner of the situation. There were also good snacks. Also, flexible baggage policy, which was great.

Cons: The boarding situation is odd and less organized or structured than any of the other airlines I've flown with.

Thu, Oct 3
MDW
Chicago Midway
OAJ
Jacksonville Albert J Ellis
5h 33m
Mon, Oct 7
OAJ
Jacksonville Albert J Ellis
MDW
Chicago Midway
6h 15m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 26,222 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.5
ATL
MYR
Excellent 10.0

Pros: Awesome crew

Cons: More room

DEN
MSP
Excellent 9.3

Pros: In flight entertainment

Cons: Food provided, other than snacks, would be a plus

LAS
BOS
Excellent 10.0

Pros: Nice plane, good service and pilots, great landing - no issues at all.

MSP
BOS
Okay 5.0

Cons: Flight attendant in First class was visibly frustrated and unfriendly. He was not helping with my simple request for a blanket. Also, the were no food service in first class.

RSW
ATL
Good 6.6

Pros: The B757

Cons: The time to switch plane it was too short almost missed the plane

Thu, Oct 3
MDW
Chicago Midway
OAJ
Jacksonville Albert J Ellis
5h 19m
Sun, Oct 6
OAJ
Jacksonville Albert J Ellis
MDW
Chicago Midway
5h 42m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 26,222 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.5
MIA
JFK
Excellent 10.0

Pros: I loved being upgraded to first class and the crew was so attentive.

Cons: Nothing, glad this was a better experience than the trip to Miami.

MSP
PSC
Excellent 10.0

Pros: The crew was great.

Cons: More food.

SEA
ATL
Excellent 10.0

Cons: Roomier

SLC
PHL
Okay 4.3

Cons: We left Salt Lake City so late that I missed all my train connections and ruined my plans.

JFK
SYR
Excellent 9.0

Cons: Great flight but old regional jet

Fri, Oct 4
MDW
Chicago Midway
OAJ
Jacksonville Albert J Ellis
6h 29m
Mon, Oct 7
OAJ
Jacksonville Albert J Ellis
MDW
Chicago Midway
6h 15m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 26,222 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.5
SLC
BNA
Excellent 9.6

Pros: Crew was great, seats were comfy and the entertainment options were good.

Cons: Flight was delayed but it happens.

SJU
ATL
Excellent 9.3

Pros: Great comfortable seats

Cons: Crowds in airport

LHR
JFK
Excellent 8.0

Pros: Food was great. Movie selection was good.

Cons: When we booked our flight, we were not informed by KAYAK that we have to pay for our luggage! I t was very unpleasant surprise both ways.

MLB
ATL
Good 6.0

Pros: Delayed, packed, bought a sandwich! Good sandwiches!

Cons: Packed and delayed

JFK
AUS
Excellent 8.0

Pros: Crew was absolutely amazing!

Cons: Delta check in was HORRIBLE! I was charged for a bag check in and had to take my bag through security and they threw away my cologne and razors.

Sat, Sep 28
MDW
Chicago Midway
OAJ
Jacksonville Albert J Ellis
5h 13m
Fri, Oct 4
OAJ
Jacksonville Albert J Ellis
MDW
Chicago Midway
6h 51m
Trip: 7 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 26,222 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.5
MCI
BOS
Okay 4.0

Cons: It was ridiculously cold for 2 1/2 hours. When my seat mate asked for a blanket, the stewardess said she only had one more - then walked off. For drinks, they skipped several people. I had to catch her eye to ask for one and then ask her to get my kids a drink in front of me.

JFK
AUS
Excellent 8.0

Pros: Crew was absolutely amazing!

Cons: Delta check in was HORRIBLE! I was charged for a bag check in and had to take my bag through security and they threw away my cologne and razors.

SAV
JFK
Good 7.6

Pros: Courteous crew.

FLL
ATL
Good 6.6

Cons: Check your planes thoroughly before placing passengers on it. The pressurized cabin almost killed us!!

JFK
SYR
Excellent 9.0

Cons: Great flight but old regional jet

Fri, Oct 11
MDW
Chicago Midway
OAJ
Jacksonville Albert J Ellis
5h 19m
Mon, Oct 14
OAJ
Jacksonville Albert J Ellis
MDW
Chicago Midway
4h 23m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 26,222 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.5
GRR
MSP
Excellent 10.0

Cons: Food offered in first

JFK
SYR
Excellent 9.0

Cons: Great flight but old regional jet

MSY
ATL
Excellent 10.0

Pros: They were awesome

Cons: Nothing I was at my best on the best airline and crew

ATL
EZE
Okay 4.0

Cons: My wife and I couldn't sit together regarless of how much money we wished to spend on reserving seats.

ATL
PHL
Good 6.8

Pros: Standard boarding The plane was on time

Cons: Better boarding process.Such as the one used by Southwest

Sat, Aug 31
MDW
Chicago Midway
OAJ
Jacksonville Albert J Ellis
6h 03m
Wed, Sep 4
OAJ
Jacksonville Albert J Ellis
MDW
Chicago Midway
6h 15m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 26,222 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.5
DTW
CDG
Good 6.0

Pros: The flight was safe and efficient.

Cons: The seats on the 787 Dreamliner proved to be uncomfortable AGAIN this trip. 2 years ago we flew the 787 overnight and the seats were the same. Hard cushions, tight seat pitch, and little room to move about.

SLC
BNA
Excellent 9.6

Pros: Crew was great, seats were comfy and the entertainment options were good.

Cons: Flight was delayed but it happens.

TRI
ATL
Mediocre 2.6

Pros: no very poor , terrible plans and plane service

Cons: better aircraft, better trained staff from delta service in tei cities wonderful fred

BNA
ATL
Okay 4.0

Pros: The crew was pleasant and helpful.

Cons: The plane was an outdated jalopy. I thought the exit doors were going to fly off. This was in vast contrast to the 737 plane that we had taken earlier in the day for a flight from BNA to ATL.

LHR
JFK
Excellent 9.3

Cons: KAYAK did not informed us we have to pay for our luggage!

Fri, Aug 30
MDW
Chicago Midway
OAJ
Jacksonville Albert J Ellis
5h 41m
Mon, Sep 23
OAJ
Jacksonville Albert J Ellis
MDW
Chicago Midway
5h 37m
Trip: 25 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 26,222 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.5
LHR
DTW
Excellent 8.0

Pros: The A330 was comfortable and the crew was efficient and cheerful.

Cons: Delta is the best experience we've had of late.

LHR
JFK
Excellent 8.0

Pros: Food was great. Movie selection was good.

Cons: When we booked our flight, we were not informed by KAYAK that we have to pay for our luggage! I t was very unpleasant surprise both ways.

LAS
BOS
Excellent 10.0

Pros: Nice plane, good service and pilots, great landing - no issues at all.

TRI
ATL
Mediocre 2.6

Pros: no very poor , terrible plans and plane service

Cons: better aircraft, better trained staff from delta service in tei cities wonderful fred

JFK
FCO
Good 7.6

Cons: Always need more room

Thu, Aug 22
MDW
Chicago Midway
OAJ
Jacksonville Albert J Ellis
5h 19m
Mon, Aug 26
OAJ
Jacksonville Albert J Ellis
MDW
Chicago Midway
5h 37m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 26,222 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.5
PWM
DTW
Mediocre 2.0

Cons: DTW to FLL, plane was delayed coming from BOS to DTW 5 hours for BOS weather. The plane arrived & they announced they would turn it around ASAP. They started the boarding process & then stopped it stating that a crew member had timed out. Delayed hour to FIND one. Shortly after delayed overnight.

DCA
JFK
Excellent 10.0

Pros: Comfy

Cons: Seats a lil tight

JFK
FCO
Good 7.6

Cons: Always need more room

BOS
AMS
Good 7.0

Cons: Better allergy aware food.

DTW
CDG
Good 6.0

Pros: The flight was safe and efficient.

Cons: The seats on the 787 Dreamliner proved to be uncomfortable AGAIN this trip. 2 years ago we flew the 787 overnight and the seats were the same. Hard cushions, tight seat pitch, and little room to move about.

Fri, Aug 23
MDW
Chicago Midway
OAJ
Jacksonville Albert J Ellis
5h 19m
Mon, Aug 26
OAJ
Jacksonville Albert J Ellis
MDW
Chicago Midway
6h 10m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 26,222 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.5
JFK
SYR
Excellent 9.0

Cons: Great flight but old regional jet

MBJ
JFK
Excellent 10.0

Cons: They were great

SLC
BNA
Excellent 9.6

Pros: Crew was great, seats were comfy and the entertainment options were good.

Cons: Flight was delayed but it happens.

ATL
PHL
Good 6.8

Pros: Standard boarding The plane was on time

Cons: Better boarding process.Such as the one used by Southwest

GSP
LGA
Okay 4.6

Pros: We got home safely! The crew was great and generally cheerful despite less than great conditions.

Cons: Lots of delays due to weather, which I get. The plane was small and old and stuffy with too close seats.

Thu, Aug 22
MDW
Chicago Midway
OAJ
Jacksonville Albert J Ellis
5h 19m
Sun, Aug 25
OAJ
Jacksonville Albert J Ellis
MDW
Chicago Midway
4h 28m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 26,222 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.5
JFK
ATL
Excellent 10.0

Pros: everything

ATL
PHL
Good 6.8

Pros: Standard boarding The plane was on time

Cons: Better boarding process.Such as the one used by Southwest

SLC
PHL
Okay 4.3

Cons: We left Salt Lake City so late that I missed all my train connections and ruined my plans.

YYZ
MSP
Mediocre 2.8

Pros: non stop flight

Cons: Crowded, small plane. No air after people had boarded while fuel was being replenished (dangerous?), sitting at gate for 20minutes. This, after a 2 hour delay. Then a rough landing in Minneapolis- plane brakes sharply and suddenly, shuddered to a taxi rate of speed. simple snacks, not very good.

JFK
PHX
Okay 4.0

Pros: Service was ok not a big deal. Could've had a accommodate us for the 2 hour delay

Cons: 2 hour delay...and once in seat it was too hot with traffic of planes in front of us.

Sat, Aug 31
MDW
Chicago Midway
OAJ
Jacksonville Albert J Ellis
6h 03m
Tue, Sep 3
OAJ
Jacksonville Albert J Ellis
MDW
Chicago Midway
7h 01m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 26,222 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.5
DCA
JFK
Excellent 10.0

Pros: Comfy

Cons: Seats a lil tight

MSP
PSC
Excellent 10.0

Pros: The crew was great.

Cons: More food.

JFK
AUS
Excellent 8.0

Pros: Crew was absolutely amazing!

Cons: Delta check in was HORRIBLE! I was charged for a bag check in and had to take my bag through security and they threw away my cologne and razors.

DTW
ORD
Good 6.0

Pros: The fight was very professionally carried out.

Cons: The gate agent hurried ineffectively to board our slightly delayed flight (around 10 min). She left open the Priority Lane and boarded all pax there, having to step 4 steps to the left to scan every boarding pass.

ATL
JFK
Mediocre 2.0

Pros: 48 hours travel from Europe Thanks to sucky Delta airlines that are absolutely the most horrible company Never ever again

Fri, Aug 30
MDW
Chicago Midway
OAJ
Jacksonville Albert J Ellis
5h 41m
Sat, Sep 21
OAJ
Jacksonville Albert J Ellis
MDW
Chicago Midway
6h 25m
Trip: 23 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 26,222 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.5
BOS
AMS
Good 7.0

Cons: Better allergy aware food.

LHR
JFK
Excellent 9.3

Cons: KAYAK did not informed us we have to pay for our luggage!

SJU
ATL
Excellent 9.3

Pros: Great comfortable seats

Cons: Crowds in airport

SAV
JFK
Good 7.6

Pros: Courteous crew.

MBJ
JFK
Excellent 10.0

Cons: They were great

Fri, Aug 30
MDW
Chicago Midway
OAJ
Jacksonville Albert J Ellis
5h 41m
Mon, Sep 2
OAJ
Jacksonville Albert J Ellis
MDW
Chicago Midway
5h 37m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 26,222 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.5
LHR
JFK
Excellent 8.0

Pros: Food was great. Movie selection was good.

Cons: When we booked our flight, we were not informed by KAYAK that we have to pay for our luggage! I t was very unpleasant surprise both ways.

RSW
ATL
Good 6.6

Pros: The B757

Cons: The time to switch plane it was too short almost missed the plane

BOS
AMS
Good 7.0

Cons: Better allergy aware food.

DTW
CDG
Good 6.0

Pros: The flight was safe and efficient.

Cons: The seats on the 787 Dreamliner proved to be uncomfortable AGAIN this trip. 2 years ago we flew the 787 overnight and the seats were the same. Hard cushions, tight seat pitch, and little room to move about.

XNA
MSP
Excellent 10.0

Pros: The crew was great.

Cons: More food.

Wed, Nov 27
MDW
Chicago Midway
OAJ
Jacksonville Albert J Ellis
6h 32m
Sun, Dec 1
OAJ
Jacksonville Albert J Ellis
MDW
Chicago Midway
4h 32m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 26,222 reviews
Overall
8.1
Boarding
8.1
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.5
LAS
BOS
Excellent 10.0

Pros: Nice plane, good service and pilots, great landing - no issues at all.

SLC
PHL
Okay 4.3

Cons: We left Salt Lake City so late that I missed all my train connections and ruined my plans.

YYZ
MSP
Mediocre 2.8

Pros: non stop flight

Cons: Crowded, small plane. No air after people had boarded while fuel was being replenished (dangerous?), sitting at gate for 20minutes. This, after a 2 hour delay. Then a rough landing in Minneapolis- plane brakes sharply and suddenly, shuddered to a taxi rate of speed. simple snacks, not very good.

RSW
ATL
Good 6.6

Pros: The B757

Cons: The time to switch plane it was too short almost missed the plane

DEN
MSP
Excellent 9.3

Pros: In flight entertainment

Cons: Food provided, other than snacks, would be a plus

*
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