Find Flights Tickets and Deals on JetBlue to Chicago from $59

Cheap Flight Tickets to Chicago

$

Boston (BOS)to

Chicago (ORD)
Depart 02/28/2026
from
$59
Seen: 18 hrs ago
one-way
Core

New York (JFK)to

Chicago (ORD)
Depart 02/23/2026
from
$74
Seen: 21 hrs ago
one-way
Core

San Juan (SJU)to

Chicago (ORD)
Depart 02/28/2026
from
$158
Seen: 22 hrs ago
one-way
Core

Orlando (MCO)to

Chicago (ORD)
Depart 02/06/2026
from
$168
Seen: 23 hrs ago
one-way
Core

Fort Lauderdale (FLL)to

Chicago (ORD)
Depart 02/06/2026
from
$151
Seen: 14 hrs ago
one-way
Core

San Francisco (SFO)to

Chicago (ORD)
Depart 02/06/2026
from
$327
Seen: 13 hrs ago
one-way
Core

Los Angeles (LAX)to

Chicago (ORD)
Depart 02/18/2026
from
$191
Seen: 7 hrs ago
one-way
Core

Washington, D.C. (DCA)to

Chicago (ORD)
Depart 02/01/2026
from
$318
Seen: 20 hrs ago
one-way
Core

Tampa (TPA)to

Chicago (ORD)
Depart 02/07/2026
from
$150
Seen: 10 hrs ago
one-way
Core

West Palm Beach (PBI)to

Chicago (ORD)
Depart 02/01/2026
from
$257
Seen: 18 hrs ago
one-way
Core

Las Vegas (LAS)to

Chicago (ORD)
Depart 02/02/2026
from
$522
Seen: 18 hrs ago
one-way
Core

Fort Myers (RSW)to

Chicago (ORD)
Depart 02/14/2026
from
$157
Seen: 15 hrs ago
one-way
Core

Raleigh/Durham (RDU)to

Chicago (ORD)
Depart 02/01/2026
from
$426
Seen: 4 hrs ago
one-way
Core

Buffalo (BUF)to

Chicago (ORD)
Depart 02/06/2026
from
$143
Seen: 22 hrs ago
one-way
Core

Jacksonville (JAX)to

Chicago (ORD)
Depart 02/13/2026
from
$272
Seen: 16 hrs ago
one-way
Core

Atlanta (ATL)to

Chicago (ORD)
Depart 02/05/2026
from
$406
Seen: 9 hrs ago
one-way
Core

Phoenix (PHX)to

Chicago (ORD)
Depart 02/25/2026
from
$147
Seen: 23 hrs ago
one-way
Core

Santo Domingo (SDQ)to

Chicago (ORD)
Depart 02/11/2026
from
$296
Seen: 19 hrs ago
one-way
Core

New Orleans (MSY)to

Chicago (ORD)
Depart 01/31/2026
from
$212
Seen: 16 hrs ago
one-way
Core

Santiago (STI)to

Chicago (ORD)
Depart 02/05/2026
from
$482
Seen: 22 hrs ago
one-way
Core

*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.

Best Cheap Flights to Chicago by Popularity

$
Best Cheap Flights to Chicago by Popularity
From
To
Fare Type
Dates
Price
Boston (BOS)Chicago (ORD)one-way
/
Core		Depart 03/05/2026

from

$59

Seen: 19 hrs ago

New York (JFK)Chicago (ORD)one-way
/
Core		Depart 05/10/2026

from

$69

Seen: 12 hrs ago

West Palm Beach (PBI)Chicago (ORD)one-way
/
Core		Depart 03/19/2026

from

$101

Seen: 9 hrs ago

Washington, D.C. (DCA)Chicago (ORD)one-way
/
Core		Depart 03/09/2026

from

$109

Seen: 22 hrs ago

Fort Lauderdale (FLL)Chicago (ORD)one-way
/
Core		Depart 11/07/2026

from

$176

Seen: 21 hrs ago

Las Vegas (LAS)Chicago (ORD)one-way
/
Core		Depart 03/04/2026

from

$182

Seen: 13 hrs ago

Richmond (RIC)Chicago (ORD)one-way
/
Core		Depart 06/05/2026

from

$188

Seen: 11 hrs ago

Los Angeles (LAX)Chicago (ORD)one-way
/
Core		Depart 03/09/2026

from

$190

Seen: 23 hrs ago

Orlando (MCO)Chicago (ORD)one-way
/
Core		Depart 06/02/2026

from

$192

Seen: 8 hrs ago

San Juan (SJU)Chicago (ORD)one-way
/
Core		Depart 03/12/2026

from

$210

Seen: 21 hrs ago

Raleigh/Durham (RDU)Chicago (ORD)one-way
/
Core		Depart 07/06/2026

from

$252

Seen: 28 minutes ago

Tampa (TPA)Chicago (ORD)one-way
/
Core		Depart 04/27/2026

from

$317

Seen: 14 hrs ago

Santo Domingo (SDQ)Chicago (ORD)one-way
/
Core		Depart 06/04/2026

from

$401

Seen: 11 hrs ago

Buffalo (BUF)Chicago (ORD)one-way
/
Core		Depart 05/08/2026

from

$457

Seen: 20 hrs ago

San Francisco (SFO)Chicago (ORD)one-way
/
Core		Depart 06/22/2026

from

$527

Seen: 13 hrs ago

Grenada (GND)Chicago (ORD)one-way
/
Core		Depart 05/04/2026

from

$534

Seen: 3 hrs ago

Punta Cana (PUJ)Chicago (ORD)one-way
/
Core		Depart 04/09/2026

from

$588

Seen: 11 hrs ago

Aguadilla (BQN)Chicago (ORD)one-way
/
Core		Depart 06/17/2026

from

$675

Seen: 14 hrs ago

Cancún (CUN)Chicago (ORD)one-way
/
Core		Depart 04/02/2026

from

$810

Seen: 22 hrs ago

New Orleans (MSY)Chicago (ORD)one-way
/
Core		Depart 04/10/2026

from

$1,016

Seen: 10 hrs ago

*Fares displayed have been collected within the last 48hrs and may no longer be available at time of booking.

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