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Flight Deals from Costa Rica to Chicago from $267

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Top Deals on flights from San Jose to Chicago

San Jose, CR (SJO) - Chicago, US (CHI)

Spirit Airlines Logo
Spirit Airlines

May 22

SJO
11h 57m
MCO

May 22

ORD
Spirit Airlines Logo
Spirit Airlines

May 27

ORD
6h 28m
FLL

May 27

SJO

as low as

$267

San Jose, CR (SJO) - Chicago, US (CHI)

Spirit Airlines Logo
Spirit Airlines

May 22

SJO
11h 1m
FLL
MCO

May 22

ORD
Spirit Airlines Logo
Spirit Airlines

May 27

ORD
6h 28m
FLL

May 27

SJO

as low as

$313

San Jose, CR (SJO) - Chicago, US (CHI)

Frontier Airlines Logo
Frontier Airlines

May 24

SJO
11h 2m
ATL

May 25

ORD
Frontier Airlines Logo
Frontier Airlines

Jun 7

ORD
7h 30m
ATL

Jun 7

SJO

as low as

$387

San Jose, CR (SJO) - Chicago, US (CHI)

United Airlines Logo
United Airlines

May 24

SJO
6h 34m
Direct

May 24

ORD
United Airlines Logo
United Airlines

Jun 7

ORD
12h 31m
IAH

Jun 8

SJO

as low as

$434

San Jose, CR (SJO) - Chicago, US (CHI)

COPA Airlines Logo
COPA Airlines

May 22

SJO
18h 42m
PTY

May 23

ORD
COPA Airlines Logo
COPA Airlines

May 27

ORD
8h 28m
PTY

May 27

SJO

as low as

$448

San Jose, CR (SJO) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

May 24

SJO
8h 47m
ATL

May 24

ORD
Delta Air Lines Logo
Delta Air Lines

Jun 7

ORD
7h 35m
ATL

Jun 7

SJO

as low as

$484

San Jose, CR (SJO) - Chicago, US (CHI)

American Airlines Logo
American Airlines

May 12

SJO
9h 35m
DFW

May 13

ORD
American Airlines Logo
American Airlines

May 14

ORD
16h 3m
MIA

May 15

SJO

as low as

$523

San Jose, CR (SJO) - Chicago, US (CHI)

JetBlue Logo
JetBlue

Jun 2

SJO
24h 54m
JFK

Jun 3

ORD
JetBlue Logo
JetBlue

Jun 5

ORD
15h 59m
BOS
MCO

Jun 6

SJO

as low as

$539

San Jose, CR (SJO) - Chicago, US (CHI)

AVIANCA Logo
AVIANCA

Jun 5

SJO
11h
SAL

Jun 5

ORD
AVIANCA Logo
AVIANCA

Jun 10

ORD
6h 10m
SAL

Jun 10

SJO

as low as

$548

San Jose, CR (SJO) - Chicago, US (CHI)

United Airlines Logo
United Airlines

May 24

SJO
6h 34m
Direct

May 24

ORD
United Airlines Logo
United Airlines

Jun 7

ORD
4h 14m
Direct

Jun 7

SJO

as low as

$551

San Jose, CR (SJO) - Chicago, US (CHI)

AVIANCA Logo
AVIANCA

May 18

SJO
20h 30m
BOG

May 19

ORD
AVIANCA Logo
AVIANCA

Jun 1

ORD
6h 5m
Direct

Jun 1

SJO

as low as

$582

San Jose, CR (SJO) - Chicago, US (CHI)

AVIANCA Logo
AVIANCA

May 18

SJO
20h 30m
BOG

May 19

ORD
AVIANCA Logo
AVIANCA

Jun 1

ORD
7h 30m
GUA

Jun 1

SJO

as low as

$595

Top Deals on flights from Liberia to Chicago

Liberia, CR (LIR) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

Aug 20

LIR
10h 30m
ATL

Aug 20

ORD
Delta Air Lines Logo
Delta Air Lines

Sep 3

ORD
6h
ATL

Sep 3

LIR

as low as

$424

Liberia, CR (LIR) - Chicago, US (CHI)

United Airlines Logo
United Airlines

Aug 20

LIR
9h 21m
IAH

Aug 20

ORD
United Airlines Logo
United Airlines

Sep 3

ORD
15h 5m
IAH

Sep 4

LIR

as low as

$487

Liberia, CR (LIR) - Chicago, US (CHI)

United Airlines Logo
United Airlines

Aug 12

LIR
17h 4m
EWR

Aug 13

ORD
United Airlines Logo
United Airlines

Aug 26

ORD
16h 25m
IAH

Aug 27

LIR

as low as

$487

Liberia, CR (LIR) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Aug 20

LIR
11h 7m
MIA

Aug 20

ORD
American Airlines Logo
American Airlines

Sep 3

ORD
6h 15m
MIA

Sep 3

LIR

as low as

$498

Liberia, CR (LIR) - Chicago, US (CHI)

Delta Air Lines Logo
Delta Air Lines

Aug 24

LIR
10h 30m
ATL

Aug 24

ORD
Delta Air Lines Logo
Delta Air Lines

Sep 7

ORD
6h
ATL

Sep 7

LIR

as low as

$508

Liberia, CR (LIR) - Chicago, US (CHI)

United Airlines Logo
United Airlines

Aug 11

LIR
17h 4m
EWR

Aug 12

ORD
United Airlines Logo
United Airlines

Aug 25

ORD
16h 25m
IAH

Aug 26

LIR

as low as

$571

Liberia, CR (LIR) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Aug 18

LIR
11h 13m
CLT

Aug 18

ORD
American Airlines Logo
American Airlines

Sep 1

ORD
6h 15m
CLT

Sep 1

LIR

as low as

$592

Liberia, CR (LIR) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Aug 24

LIR
10h
DFW

Aug 24

ORD
American Airlines Logo
American Airlines

Sep 7

ORD
16h 25m
DFW

Sep 8

LIR

as low as

$598

Liberia, CR (LIR) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Aug 15

LIR
27h 21m
CLT

Aug 16

ORD
American Airlines Logo
American Airlines

Aug 25

ORD
8h 5m
CLT
MIA

Aug 25

LIR

as low as

$660

Liberia, CR (LIR) - Chicago, US (CHI)

American Airlines Logo
American Airlines

Aug 14

LIR
29h 5m
MIA

Aug 15

ORD
American Airlines Logo
American Airlines

Aug 22

ORD
8h 5m
CLT
MIA

Aug 22

LIR

as low as

$686

Liberia, CR (LIR) - Chicago, US (CHI)

JetBlue Logo
JetBlue

Aug 15

LIR
20h 35m
JFK

Aug 16

ORD
JetBlue Logo
JetBlue

Aug 25

ORD
18h 49m
BOS
JFK

Aug 26

LIR

as low as

$724

Liberia, CR (LIR) - Chicago, US (CHI)

JetBlue Logo
JetBlue

Aug 14

LIR
21h 2m
JFK

Aug 15

ORD
JetBlue Logo
JetBlue

Aug 22

ORD
25h 10m
JFK

Aug 23

LIR

as low as

$954

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