background

Flight Deals from Chicago to Costa Rica from $271

Bundle + Save

Bundle + Save

Top flight deals from leading airlines:

LH LogoLX LogoDL LogoAS LogoUA LogoAC LogoB6 Logo

... and +100s more

Incredible Deals

Save up to 50% on select flights with Priceline

Bundle & Save

Save an average of $240 per person when bundling your flight and hotel together with Priceline

Best Price Guarantee

If a VIP member finds a better price elsewhere, we'll refund up to 200% of the difference

Help 24/7

We’re always here for you - reach us 24 hours a day, 7 days a week

Phone Banner

Priceline Phone Deals

Book with an agent for great rates!

Top Deals on flights from Chicago to San Jose

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

Spirit Airlines Logo
Spirit Airlines

Jun 10

ORD
26h 50m
MCO

Jun 11

SJO
Spirit Airlines Logo
Spirit Airlines

Jun 17

SJO
31h 12m
MCO

Jun 18

ORD

as low as

$271

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

Spirit Airlines Logo
Spirit Airlines

Jun 10

ORD
38h 5m
IAH
FLL

Jun 12

SJO
Spirit Airlines Logo
Spirit Airlines

Jun 17

SJO
31h 12m
MCO

Jun 18

ORD

as low as

$282

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

TACA Logo
TACA

Jun 11

ORD
7h 30m
GUA

Jun 11

SJO
TACA Logo
TACA

Jun 17

SJO
22h 5m
GUA

Jun 18

ORD

as low as

$345

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

TACA Logo
TACA

Jun 11

ORD
16h 55m
GUA
SAL

Jun 12

SJO
TACA Logo
TACA

Jun 17

SJO
22h 5m
GUA

Jun 18

ORD

as low as

$347

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

AVIANCA Logo
AVIANCA

Jun 10

ORD
6h 10m
SAL

Jun 10

SJO
AVIANCA Logo
AVIANCA

Jun 17

SJO
22h 5m
GUA

Jun 18

ORD

as low as

$350

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

Spirit Airlines Logo
Spirit Airlines

Jun 12

ORD
24h 6m
ATL
MCO

Jun 13

SJO
Spirit Airlines Logo
Spirit Airlines

Jun 16

SJO
21h 54m
MCO
ATL

Jun 17

ORD

as low as

$388

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

Frontier Airlines Logo
Frontier Airlines

Jun 7

ORD
7h 30m
ATL

Jun 7

SJO
Frontier Airlines Logo
Frontier Airlines

Jun 14

SJO
10h 27m
ATL

Jun 15

ORD

as low as

$411

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

JetBlue Logo
JetBlue

May 27

ORD
20h 46m
JFK

May 28

SJO
JetBlue Logo
JetBlue

Jun 2

SJO
24h 54m
JFK

Jun 3

ORD

as low as

$440

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

American Airlines Logo
American Airlines

Jun 11

ORD
14h 9m
MIA

Jun 11

SJO
American Airlines Logo
American Airlines

Jun 17

SJO
10h 11m
DFW

Jun 18

ORD

as low as

$445

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

COPA Airlines Logo
COPA Airlines

May 27

ORD
13h 59m
PTY

May 27

SJO
COPA Airlines Logo
COPA Airlines

Jun 3

SJO
18h 42m
PTY

Jun 4

ORD

as low as

$447

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

American Airlines Logo
American Airlines

Jun 11

ORD
14h 9m
MIA

Jun 11

SJO
American Airlines Logo
American Airlines

Jun 17

SJO
11h 25m
MIA
CLT

Jun 17

ORD

as low as

$449

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

JetBlue Logo
JetBlue

May 27

ORD
29h 40m
JFK
FLL

May 28

SJO
JetBlue Logo
JetBlue

Jun 2

SJO
28h 26m
JFK
BOS

Jun 3

ORD

as low as

$456

Top Deals on flights from Chicago to Liberia

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

Delta Air Lines Logo
Delta Air Lines

Aug 26

ORD
6h
ATL

Aug 26

LIR
Delta Air Lines Logo
Delta Air Lines

Sep 9

LIR
10h 28m
ATL

Sep 9

ORD

as low as

$424

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

American Airlines Logo
American Airlines

Sep 6

ORD
16h 20m
MIA

Sep 7

LIR
American Airlines Logo
American Airlines

Sep 9

LIR
9h 39m
MIA

Sep 9

ORD

as low as

$477

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

American Airlines Logo
American Airlines

Sep 6

ORD
16h 20m
MIA

Sep 7

LIR
American Airlines Logo
American Airlines

Sep 9

LIR
18h 46m
DFW

Sep 10

ORD

as low as

$494

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

American Airlines Logo
American Airlines

Aug 26

ORD
8h 25m
MIA

Aug 26

LIR
American Airlines Logo
American Airlines

Sep 9

LIR
17h 25m
DFW

Sep 10

ORD

as low as

$494

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

Delta Air Lines Logo
Delta Air Lines

Aug 28

ORD
6h
ATL

Aug 28

LIR
Delta Air Lines Logo
Delta Air Lines

Sep 11

LIR
10h 28m
ATL

Sep 11

ORD

as low as

$504

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

United Airlines Logo
United Airlines

Aug 26

ORD
15h 5m
IAH

Aug 27

LIR
United Airlines Logo
United Airlines

Sep 9

LIR
9h 21m
IAH

Sep 9

ORD

as low as

$514

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

American Airlines Logo
American Airlines

Sep 6

ORD
8h 10m
PHL
CLT

Sep 6

LIR
American Airlines Logo
American Airlines

Sep 9

LIR
9h 39m
MIA

Sep 9

ORD

as low as

$566

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

American Airlines Logo
American Airlines

Aug 23

ORD
17h 10m
CLT

Aug 24

LIR
American Airlines Logo
American Airlines

Sep 6

LIR
9h 39m
MIA

Sep 6

ORD

as low as

$584

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

United Airlines Logo
United Airlines

Sep 3

ORD
15h 5m
IAH

Sep 4

LIR
United Airlines Logo
United Airlines

Sep 7

LIR
18h 33m
IAH

Sep 8

ORD

as low as

$594

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

United Airlines Logo
United Airlines

Aug 15

ORD
13h 20m
EWR

Aug 16

LIR
United Airlines Logo
United Airlines

Aug 29

LIR
10h 55m
IAH

Aug 30

ORD

as low as

$654

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

JetBlue Logo
JetBlue

Aug 28

ORD
18h 49m
BOS
JFK

Aug 29

LIR
JetBlue Logo
JetBlue

Sep 1

LIR
21h 2m
JFK

Sep 2

ORD

as low as

$698

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

JetBlue Logo
JetBlue

Aug 28

ORD
25h 5m
JFK

Aug 29

LIR
JetBlue Logo
JetBlue

Sep 1

LIR
21h 2m
JFK

Sep 2

ORD

as low as

$796

Priceline Phone Deals

Book with an agent for great rates!
Call now!

1 (888) 775-6158