Find Cheap Flights from Costa Rica to Chicago Midway

Search hundreds of travel sites at once for deals on flights to Chicago Midway

Tue 4/24
Tue 5/1
Any month
Compare vs. KAYAK |

Costa Rica to Chicago Midway Flight Information

Flights Arrive in Chicago Midway
Flights Depart from Costa Rica
Flight Price $414
Airlines Aeromexico, Delta, Hahn Air Systems

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

Airports
Origin
San Jose
$414
only
$414
Destination
Chicago
$414
only
$414
Wed, May 2
SJO
MDW
51h 44m
Wed, May 9
MDW
SJO
36h 30m
Trip: 8 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 6192 reviews
Overall
7.4
Boarding
7.4
Comfort
7.4
Crew
7.8
Entertainment
7.2
Food
6.9
MEX
YYZ
Mediocre 2.0

On the first leg of my trip, the time shown on the boarding pass was the time I needed to be at the gate. For this leg of the trip, the time on the boarding pass was the time the plane left. I arrived at the gate at the time the boarding pass said and the plane had already left. I am traveling to my father's funeral and the only option I had was to rebook for an additional cost of $600. Extremely upset.

MEX
SFO
Mediocre 2.0

International flight. 5 hours. Entertainment system did not work at all for the entire plane. For the entire flight. TERRIBLE.

GDL
SMF
Excellent 10.0

The onlt airline providing every pasanger with Free drinks and food. Live the beer and mix Tequila drinks.

I did not like paying $50 us for the second bag i thing $ 25 its ok 50 its to much... I need ir to Boeing chese and tequila so my carry on bag tas over waigt so i check ir in.

CUN
GDL
Mediocre 2.0

Not organized enough. Had to rush to second flight because 1st flight was delayed

MIA
MEX
Good 6.0

No spacefor carry on bag

Wed, May 16
SJO
MDW
9h 21m
Tue, May 22
MDW
SJO
6h 58m
Trip: 7 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 17515 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
AUS
BOS
Excellent 9.0

Seat did not recline.

ATL
LAS
Good 6.6

Nice flight attendants

Freezing flight.

TPA
LGA
Good 6.3

No entertainment and no food other than snacks.

DEN
DTW
Good 6.3

Was unclear which zone was boarding. Legroom was comprised when passenger in immediate row ahead reclined seat early in flight.

CDG
JFK
Excellent 10.0

Staff and equipment

Early to arrive but gate not ready so we lost our edge

Thu, Jun 21
SJO
MDW
23h 40m
Mon, Jun 25
MDW
SJO
26h 17m
Trip: 5 days
6.0GoodShow reviews
Overall 6.0 Good
Based on 11 reviews
Boarding
6.7
Comfort
5.6
Crew
6.7
Entertainment
5.0
Food
5.3
VFA
JNB
Mediocre 2.0

They cancelled the flight without any reason and you sent an email the night before departure and as I was in Africa I couldn't read it. So I had to discovered it by other tourists and then I had to book another flight at a higher rate because of the time and I had to cancel a couple of activities already paid to solve all of this and they offer to reimburse just the cost of the flight in 60 days. Horrible experience

GRU
RAO
Good 6.4

Not having to change airports in Sao Paulo!

flight operated by Passaredo. Prop plane, waiting area was very basic. At checkin the rep did not want to add my AA Frequent flier number to my reservation. The flight has TAM (oneworld) flight number so I wanted to get credit but was unsuccessful.

RTB
TGU
Excellent 10.0

Flora the flight attendant. Very professional..

N/a

Sat, May 5
SJO
MDW
16h 27m
Tue, May 8
MDW
SJO
12h 20m
Trip: 4 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 6192 reviews
Overall
7.4
Boarding
7.4
Comfort
7.4
Crew
7.8
Entertainment
7.2
Food
6.9
CUN
GDL
Mediocre 2.0

Not organized enough. Had to rush to second flight because 1st flight was delayed

MEX
SFO
Mediocre 2.0

International flight. 5 hours. Entertainment system did not work at all for the entire plane. For the entire flight. TERRIBLE.

MEX
IAD
Okay 5.6

Rude crew.

SMF
GDL
Mediocre 2.0

Flight delayed 7 hrs and the official website never updated to reflect the change. Called customer service twice and they had no clue. The last representative advised to be at the airport at the original departure time to make sure we spoke to someone there. That showed a lack of knowledge and trustworthiness. The airports official website also didn’t reflect the delay.

GDL
SMF
Excellent 10.0

The onlt airline providing every pasanger with Free drinks and food. Live the beer and mix Tequila drinks.

I did not like paying $50 us for the second bag i thing $ 25 its ok 50 its to much... I need ir to Boeing chese and tequila so my carry on bag tas over waigt so i check ir in.

Tue, Apr 24
SJO
MDW
8h 14m
Fri, Apr 27
MDW
SJO
11h 52m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 17515 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
SLC
OAK
Good 7.0

The monitors kept on freezing

CDG
JFK
Excellent 10.0

Staff and equipment

Early to arrive but gate not ready so we lost our edge

ATL
LAS
Good 6.6

Nice flight attendants

Freezing flight.

TPA
LGA
Good 6.3

No entertainment and no food other than snacks.

LAX
SLC
Excellent 10.0

The crew members were very friendly

Coach seats still a little too small. Always bump the person next to me

Sat, May 12
SJO
MDW
8h 05m
Tue, May 15
MDW
SJO
6h 58m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 17515 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
TPA
LGA
Good 6.3

No entertainment and no food other than snacks.

MSP
PDX
Good 7.3

Entertainment was good and staff was pleasant

Delta assigns seats at boarding, miss when you could pick which seats you sit in. I bought my sisters ticket, hoping we would then be able to sit together but we both ended up in the middle in different rows.

SLC
OAK
Good 7.0

The monitors kept on freezing

DEN
DTW
Good 6.3

Was unclear which zone was boarding. Legroom was comprised when passenger in immediate row ahead reclined seat early in flight.

BOS
SLC
Excellent 8.0

Food was terrible, for first class they need to up the standards

Thu, May 17
SJO
MDW
9h 21m
Sun, May 20
MDW
SJO
14h 10m
Trip: 4 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 17515 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
DEN
DTW
Good 6.3

Was unclear which zone was boarding. Legroom was comprised when passenger in immediate row ahead reclined seat early in flight.

TPA
LGA
Good 6.3

No entertainment and no food other than snacks.

PUJ
DTW
Excellent 8.0

Comfortable

I was good with the flight, my friend had some allergy problems with the ac.

CDG
JFK
Excellent 10.0

Staff and equipment

Early to arrive but gate not ready so we lost our edge

MSP
PDX
Good 7.3

Entertainment was good and staff was pleasant

Delta assigns seats at boarding, miss when you could pick which seats you sit in. I bought my sisters ticket, hoping we would then be able to sit together but we both ended up in the middle in different rows.

Tue, Jun 5
SJO
MDW
15h 42m
Thu, Jul 5
MDW
SJO
50h 19m
Trip: 31 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 6192 reviews
Overall
7.4
Boarding
7.4
Comfort
7.4
Crew
7.8
Entertainment
7.2
Food
6.9
CUN
MEX
Excellent 8.6

The employees were very friendly and helpful. The seats were reasonably comfortable, but pretty short on leg room. They stayed pretty close to their schedule for takeoff and arrival. Not much for food options.

The website is the worst ever, don’t even bother.

SEA
MEX
Excellent 10.0

Excellent customer service and they actually served us delicious dinner, no pretzels nor peanuts ...very impressed !

MEX
YYZ
Mediocre 2.0

On the first leg of my trip, the time shown on the boarding pass was the time I needed to be at the gate. For this leg of the trip, the time on the boarding pass was the time the plane left. I arrived at the gate at the time the boarding pass said and the plane had already left. I am traveling to my father's funeral and the only option I had was to rebook for an additional cost of $600. Extremely upset.

SMF
GDL
Mediocre 2.0

Flight delayed 7 hrs and the official website never updated to reflect the change. Called customer service twice and they had no clue. The last representative advised to be at the airport at the original departure time to make sure we spoke to someone there. That showed a lack of knowledge and trustworthiness. The airports official website also didn’t reflect the delay.

GDL
SMF
Excellent 10.0

The onlt airline providing every pasanger with Free drinks and food. Live the beer and mix Tequila drinks.

I did not like paying $50 us for the second bag i thing $ 25 its ok 50 its to much... I need ir to Boeing chese and tequila so my carry on bag tas over waigt so i check ir in.

Tue, Oct 2
SJO
MDW
12h 29m
Tue, Oct 16
MDW
SJO
6h 46m
Trip: 15 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 17515 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
ATL
LAS
Good 6.6

Nice flight attendants

Freezing flight.

CDG
JFK
Excellent 10.0

Staff and equipment

Early to arrive but gate not ready so we lost our edge

SLC
OAK
Good 7.0

The monitors kept on freezing

BOS
SLC
Excellent 8.0

Food was terrible, for first class they need to up the standards

MSP
PDX
Good 7.3

Entertainment was good and staff was pleasant

Delta assigns seats at boarding, miss when you could pick which seats you sit in. I bought my sisters ticket, hoping we would then be able to sit together but we both ended up in the middle in different rows.

Sun, May 6
SJO
MDW
15h 42m
Wed, May 9
MDW
SJO
17h 35m
Trip: 4 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 6192 reviews
Overall
7.4
Boarding
7.4
Comfort
7.4
Crew
7.8
Entertainment
7.2
Food
6.9
SMF
GDL
Mediocre 2.0

Flight delayed 7 hrs and the official website never updated to reflect the change. Called customer service twice and they had no clue. The last representative advised to be at the airport at the original departure time to make sure we spoke to someone there. That showed a lack of knowledge and trustworthiness. The airports official website also didn’t reflect the delay.

CUN
MEX
Excellent 8.6

The employees were very friendly and helpful. The seats were reasonably comfortable, but pretty short on leg room. They stayed pretty close to their schedule for takeoff and arrival. Not much for food options.

The website is the worst ever, don’t even bother.

CUN
GDL
Mediocre 2.0

Not organized enough. Had to rush to second flight because 1st flight was delayed

GDL
SMF
Excellent 10.0

The onlt airline providing every pasanger with Free drinks and food. Live the beer and mix Tequila drinks.

I did not like paying $50 us for the second bag i thing $ 25 its ok 50 its to much... I need ir to Boeing chese and tequila so my carry on bag tas over waigt so i check ir in.

SEA
MEX
Excellent 10.0

Excellent customer service and they actually served us delicious dinner, no pretzels nor peanuts ...very impressed !

Wed, Oct 3
SJO
MDW
8h 24m
Tue, Oct 16
MDW
SJO
6h 46m
Trip: 14 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 17515 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
AUS
BOS
Excellent 9.0

Seat did not recline.

PVR
SEA
Good 7.0

Cannot. Figure out how to use the wifi.

JFK
SJU
Excellent 8.8

Flight was delayed over 1hr.

BOS
SLC
Excellent 8.0

Food was terrible, for first class they need to up the standards

DEN
DTW
Good 6.3

Was unclear which zone was boarding. Legroom was comprised when passenger in immediate row ahead reclined seat early in flight.

Fri, Oct 12
SJO
MDW
15h 19m
Mon, Oct 15
MDW
SJO
23h 20m
Trip: 4 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 6192 reviews
Overall
7.4
Boarding
7.4
Comfort
7.4
Crew
7.8
Entertainment
7.2
Food
6.9
CUN
GDL
Mediocre 2.0

Not organized enough. Had to rush to second flight because 1st flight was delayed

MIA
MEX
Good 6.0

No spacefor carry on bag

MEX
SFO
Mediocre 2.0

International flight. 5 hours. Entertainment system did not work at all for the entire plane. For the entire flight. TERRIBLE.

CUN
MEX
Excellent 8.6

The employees were very friendly and helpful. The seats were reasonably comfortable, but pretty short on leg room. They stayed pretty close to their schedule for takeoff and arrival. Not much for food options.

The website is the worst ever, don’t even bother.

MEX
IAD
Okay 5.6

Rude crew.

Wed, May 9
SJO
MDW
8h 27m
Sun, May 13
MDW
SJO
14h 10m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 17515 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
MSP
PDX
Good 7.3

Entertainment was good and staff was pleasant

Delta assigns seats at boarding, miss when you could pick which seats you sit in. I bought my sisters ticket, hoping we would then be able to sit together but we both ended up in the middle in different rows.

DEN
DTW
Good 6.3

Was unclear which zone was boarding. Legroom was comprised when passenger in immediate row ahead reclined seat early in flight.

AUS
BOS
Excellent 9.0

Seat did not recline.

PVR
SEA
Good 7.0

Cannot. Figure out how to use the wifi.

JFK
SJU
Excellent 8.8

Flight was delayed over 1hr.

Fri, Oct 12
SJO
MDW
33h 54m
Mon, Oct 15
MDW
SJO
26h 12m
Trip: 4 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 6192 reviews
Overall
7.4
Boarding
7.4
Comfort
7.4
Crew
7.8
Entertainment
7.2
Food
6.9
SFO
GDL
Excellent 10.0

I love the service The workers there really helpful and friendly

SMF
GDL
Mediocre 2.0

Flight delayed 7 hrs and the official website never updated to reflect the change. Called customer service twice and they had no clue. The last representative advised to be at the airport at the original departure time to make sure we spoke to someone there. That showed a lack of knowledge and trustworthiness. The airports official website also didn’t reflect the delay.

MIA
MEX
Good 6.0

No spacefor carry on bag

MEX
YYZ
Mediocre 2.0

On the first leg of my trip, the time shown on the boarding pass was the time I needed to be at the gate. For this leg of the trip, the time on the boarding pass was the time the plane left. I arrived at the gate at the time the boarding pass said and the plane had already left. I am traveling to my father's funeral and the only option I had was to rebook for an additional cost of $600. Extremely upset.

GDL
SMF
Excellent 10.0

The onlt airline providing every pasanger with Free drinks and food. Live the beer and mix Tequila drinks.

I did not like paying $50 us for the second bag i thing $ 25 its ok 50 its to much... I need ir to Boeing chese and tequila so my carry on bag tas over waigt so i check ir in.

Thu, Jun 7
SJO
MDW
14h 47m
Wed, Jun 27
MDW
SJO
13h 32m
Trip: 21 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 17515 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
BOS
SLC
Excellent 8.0

Food was terrible, for first class they need to up the standards

PVR
SEA
Good 7.0

Cannot. Figure out how to use the wifi.

DEN
DTW
Good 6.3

Was unclear which zone was boarding. Legroom was comprised when passenger in immediate row ahead reclined seat early in flight.

MSP
PDX
Good 7.3

Entertainment was good and staff was pleasant

Delta assigns seats at boarding, miss when you could pick which seats you sit in. I bought my sisters ticket, hoping we would then be able to sit together but we both ended up in the middle in different rows.

JFK
SJU
Excellent 8.8

Flight was delayed over 1hr.

Mon, Jun 11
SJO
MDW
10h 47m
Wed, Jun 27
MDW
SJO
13h 32m
Trip: 17 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 17515 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
ATL
LAS
Good 6.6

Nice flight attendants

Freezing flight.

MSP
PDX
Good 7.3

Entertainment was good and staff was pleasant

Delta assigns seats at boarding, miss when you could pick which seats you sit in. I bought my sisters ticket, hoping we would then be able to sit together but we both ended up in the middle in different rows.

PVR
SEA
Good 7.0

Cannot. Figure out how to use the wifi.

PUJ
DTW
Excellent 8.0

Comfortable

I was good with the flight, my friend had some allergy problems with the ac.

DEN
DTW
Good 6.3

Was unclear which zone was boarding. Legroom was comprised when passenger in immediate row ahead reclined seat early in flight.

Fri, Oct 5
SJO
MDW
8h 24m
Wed, Oct 10
MDW
SJO
14h 45m
Trip: 6 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 17515 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
CDG
JFK
Excellent 10.0

Staff and equipment

Early to arrive but gate not ready so we lost our edge

AUS
BOS
Excellent 9.0

Seat did not recline.

PVR
SEA
Good 7.0

Cannot. Figure out how to use the wifi.

PUJ
DTW
Excellent 8.0

Comfortable

I was good with the flight, my friend had some allergy problems with the ac.

ATL
LAS
Good 6.6

Nice flight attendants

Freezing flight.

Thu, Oct 4
SJO
MDW
15h 19m
Tue, Oct 9
MDW
SJO
17h 45m
Trip: 6 days
7.3GoodShow reviews
Overall 7.3 Good
Based on 6192 reviews
Overall
7.4
Boarding
7.4
Comfort
7.4
Crew
7.8
Entertainment
7.2
Food
6.9
MEX
LAX
Okay 5.6

Captain and crew were really nice Airplane was clean

Food was cheap Trip was too long 41/2 hora each way when usually takes 3 hits

SEA
MEX
Excellent 10.0

Excellent customer service and they actually served us delicious dinner, no pretzels nor peanuts ...very impressed !

CUN
GDL
Mediocre 2.0

Not organized enough. Had to rush to second flight because 1st flight was delayed

MIA
MEX
Good 6.0

The fly was good.

The experiente to arrive at Mexico City airport is always the worst one. The airplane takes much time to arrive at the finger, the lines are too big, the luggages takes much time to arrive...

MEX
IAD
Okay 5.6

Rude crew.

Tue, Apr 24
SJO
MDW
8h 14m
Thu, Apr 26
MDW
SJO
7h 05m
Trip: 3 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 17515 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
PUJ
DTW
Excellent 8.0

Comfortable

I was good with the flight, my friend had some allergy problems with the ac.

SLC
OAK
Good 7.0

The monitors kept on freezing

LAX
SLC
Excellent 10.0

The crew members were very friendly

Coach seats still a little too small. Always bump the person next to me

ATL
LAS
Good 6.6

Nice flight attendants

Freezing flight.

AUS
BOS
Excellent 9.0

Seat did not recline.

Thu, Aug 2
SJO
MDW
10h 40m
Mon, Aug 6
MDW
SJO
13h 15m
Trip: 5 days
7.9GoodShow reviews
Overall 7.9 Good
Based on 17515 reviews
Overall
8.0
Boarding
8.1
Comfort
7.8
Crew
8.4
Entertainment
7.6
Food
7.4
TPA
LGA
Good 6.3

No entertainment and no food other than snacks.

JFK
SJU
Excellent 8.8

Flight was delayed over 1hr.

MSP
PDX
Good 7.3

Entertainment was good and staff was pleasant

Delta assigns seats at boarding, miss when you could pick which seats you sit in. I bought my sisters ticket, hoping we would then be able to sit together but we both ended up in the middle in different rows.

DEN
DTW
Good 6.3

Was unclear which zone was boarding. Legroom was comprised when passenger in immediate row ahead reclined seat early in flight.

PUJ
DTW
Excellent 8.0

Comfortable

I was good with the flight, my friend had some allergy problems with the ac.

*
Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

We compile tonnes of data for you
Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
please send us an and someone from our team will get back to you promptly.