Cheap Flights to Chicago
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    Cheap Flights to Chicago

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    Spirit Airlines 9 results US$232 View Flights
    United Airlines 642 results US$236 View Flights
    Southwest Airlines 93 results US$256 View Flights
    Delta Air Lines 81 results US$273 View Flights
    American Airlines 226 results US$302 View Flights
    US Airways 99 results US$360 View Flights
    AirTran Airways 1 result US$495 View Flights
    Alaska Airlines 102 results US$495 View Flights
    Virgin America 1 result US$514 View Flights
    Frontier Airlines 3 results US$522 View Flights
    Depart:Thu, 20 Nov Return:Wed, 26 Nov New York to Chicago Thu, 20 Nov - Wed, 26 Nov
    Spirit Airlines Direct 2h 23m
    9:55 pm LGA - 11:18 pm ORD
    Southwest Airlines Direct 2h
    6:00 am MDW - 9:00 am EWR
    US$233
    fly.co.uk
    Show Details

    Depart: New York to Chicago

    LGA
    9:55 pm
    2h 23m
    ORD
    11:18 pm
    Airlines
    Flight No.
    From
    To
    Duration
    NK331
    Thu 20 Nov, 9:55 pm
    LGA New York
    Thu 20 Nov, 11:18 pm
    ORD Chicago
    2h 23m

    Return: Chicago to New York

    MDW
    6:00 am
    2h
    EWR
    9:00 am
    Airlines
    Flight No.
    From
    To
    Duration
    WN2868
    Wed 26 Nov, 6:00 am
    MDW Chicago
    Wed 26 Nov, 9:00 am
    EWR New York
    2h
    Depart:Fri, 12 Sep Return:Sun, 14 Sep Cleveland to Chicago Fri, 12 Sep - Sun, 14 Sep
    United Airlines Direct 1h 21m
    1:49 pm CLE - 2:10 pm ORD
    United Airlines Direct 1h 17m
    9:55 pm ORD - 12:12 am (+1) CLE
    US$236
    united.com
    Show Details

    Depart: Cleveland to Chicago

    CLE
    1:49 pm
    1h 21m
    ORD
    2:10 pm
    Airlines
    Flight No.
    From
    To
    Duration
    UA279
    Fri 12 Sep, 1:49 pm
    CLE Cleveland
    Fri 12 Sep, 2:10 pm
    ORD Chicago
    1h 21m

    Return: Chicago to Cleveland

    ORD
    9:55 pm
    1h 17m
    CLE
    12:12 am (+1)
    Airlines
    Flight No.
    From
    To
    Duration
    UA230
    Sun 14 Sep, 9:55 pm
    ORD Chicago
    Mon 15 Sep, 12:12 am
    CLE Cleveland
    1h 17m
    Depart:Fri, 12 Sep Return:Sun, 14 Sep Cleveland to Chicago Fri, 12 Sep - Sun, 14 Sep
    United Airlines Direct 1h 20m
    3:46 pm CLE - 4:06 pm ORD
    United Airlines Direct 1h 17m
    9:55 pm ORD - 12:12 am (+1) CLE
    US$236
    united.com
    Show Details

    Depart: Cleveland to Chicago

    CLE
    3:46 pm
    1h 20m
    ORD
    4:06 pm
    Airlines
    Flight No.
    From
    To
    Duration
    UA236
    Fri 12 Sep, 3:46 pm
    CLE Cleveland
    Fri 12 Sep, 4:06 pm
    ORD Chicago
    1h 20m

    Return: Chicago to Cleveland

    ORD
    9:55 pm
    1h 17m
    CLE
    12:12 am (+1)
    Airlines
    Flight No.
    From
    To
    Duration
    UA230
    Sun 14 Sep, 9:55 pm
    ORD Chicago
    Mon 15 Sep, 12:12 am
    CLE Cleveland
    1h 17m
    Depart:Fri, 12 Sep Return:Sun, 14 Sep Cleveland to Chicago Fri, 12 Sep - Sun, 14 Sep
    United Airlines Direct 1h 20m
    3:46 pm CLE - 4:06 pm ORD
    United Airlines Direct 1h 17m
    8:45 am ORD - 11:02 am CLE
    US$236
    united.com
    Show Details

    Depart: Cleveland to Chicago

    CLE
    3:46 pm
    1h 20m
    ORD
    4:06 pm
    Airlines
    Flight No.
    From
    To
    Duration
    UA236
    Fri 12 Sep, 3:46 pm
    CLE Cleveland
    Fri 12 Sep, 4:06 pm
    ORD Chicago
    1h 20m

    Return: Chicago to Cleveland

    ORD
    8:45 am
    1h 17m
    CLE
    11:02 am
    Airlines
    Flight No.
    From
    To
    Duration
    UA3469
    Sun 14 Sep, 8:45 am
    ORD Chicago
    Sun 14 Sep, 11:02 am
    CLE Cleveland
    1h 17m
    Depart:Fri, 12 Sep Return:Sun, 14 Sep Cleveland to Chicago Fri, 12 Sep - Sun, 14 Sep
    United Airlines Direct 1h 20m
    3:46 pm CLE - 4:06 pm ORD
    United Airlines Direct 1h 18m
    7:30 am ORD - 9:48 am CLE
    US$236
    united.com
    Show Details

    Depart: Cleveland to Chicago

    CLE
    3:46 pm
    1h 20m
    ORD
    4:06 pm
    Airlines
    Flight No.
    From
    To
    Duration
    UA236
    Fri 12 Sep, 3:46 pm
    CLE Cleveland
    Fri 12 Sep, 4:06 pm
    ORD Chicago
    1h 20m

    Return: Chicago to Cleveland

    ORD
    7:30 am
    1h 18m
    CLE
    9:48 am
    Airlines
    Flight No.
    From
    To
    Duration
    UA410
    Sun 14 Sep, 7:30 am
    ORD Chicago
    Sun 14 Sep, 9:48 am
    CLE Cleveland
    1h 18m
    Depart:Fri, 12 Sep Return:Sun, 14 Sep Cleveland to Chicago Fri, 12 Sep - Sun, 14 Sep
    United Airlines Direct 1h 23m
    6:00 am CLE - 6:23 am ORD
    United Airlines Direct 1h 17m
    8:45 am ORD - 11:02 am CLE
    US$236
    united.com
    Show Details

    Depart: Cleveland to Chicago

    CLE
    6:00 am
    1h 23m
    ORD
    6:23 am
    Airlines
    Flight No.
    From
    To
    Duration
    UA3520
    Fri 12 Sep, 6:00 am
    CLE Cleveland
    Fri 12 Sep, 6:23 am
    ORD Chicago
    1h 23m

    Return: Chicago to Cleveland

    ORD
    8:45 am
    1h 17m
    CLE
    11:02 am
    Airlines
    Flight No.
    From
    To
    Duration
    UA3469
    Sun 14 Sep, 8:45 am
    ORD Chicago
    Sun 14 Sep, 11:02 am
    CLE Cleveland
    1h 17m
    Depart:Fri, 12 Sep Return:Sun, 14 Sep Cleveland to Chicago Fri, 12 Sep - Sun, 14 Sep
    United Airlines Direct 1h 21m
    1:49 pm CLE - 2:10 pm ORD
    United Airlines Direct 1h 17m
    8:45 am ORD - 11:02 am CLE
    US$236
    united.com
    Show Details

    Depart: Cleveland to Chicago

    CLE
    1:49 pm
    1h 21m
    ORD
    2:10 pm
    Airlines
    Flight No.
    From
    To
    Duration
    UA279
    Fri 12 Sep, 1:49 pm
    CLE Cleveland
    Fri 12 Sep, 2:10 pm
    ORD Chicago
    1h 21m

    Return: Chicago to Cleveland

    ORD
    8:45 am
    1h 17m
    CLE
    11:02 am
    Airlines
    Flight No.
    From
    To
    Duration
    UA3469
    Sun 14 Sep, 8:45 am
    ORD Chicago
    Sun 14 Sep, 11:02 am
    CLE Cleveland
    1h 17m
    Depart:Fri, 12 Sep Return:Sun, 14 Sep Cleveland to Chicago Fri, 12 Sep - Sun, 14 Sep
    United Airlines Direct 1h 23m
    6:00 am CLE - 6:23 am ORD
    United Airlines Direct 1h 18m
    7:30 am ORD - 9:48 am CLE
    US$236
    united.com
    Show Details

    Depart: Cleveland to Chicago

    CLE
    6:00 am
    1h 23m
    ORD
    6:23 am
    Airlines
    Flight No.
    From
    To
    Duration
    UA3520
    Fri 12 Sep, 6:00 am
    CLE Cleveland
    Fri 12 Sep, 6:23 am
    ORD Chicago
    1h 23m

    Return: Chicago to Cleveland

    ORD
    7:30 am
    1h 18m
    CLE
    9:48 am
    Airlines
    Flight No.
    From
    To
    Duration
    UA410
    Sun 14 Sep, 7:30 am
    ORD Chicago
    Sun 14 Sep, 9:48 am
    CLE Cleveland
    1h 18m
    Depart:Fri, 12 Sep Return:Sun, 14 Sep Cleveland to Chicago Fri, 12 Sep - Sun, 14 Sep
    United Airlines Direct 1h 21m
    1:49 pm CLE - 2:10 pm ORD
    United Airlines Direct 1h 18m
    7:30 am ORD - 9:48 am CLE
    US$236
    united.com
    Show Details

    Depart: Cleveland to Chicago

    CLE
    1:49 pm
    1h 21m
    ORD
    2:10 pm
    Airlines
    Flight No.
    From
    To
    Duration
    UA279
    Fri 12 Sep, 1:49 pm
    CLE Cleveland
    Fri 12 Sep, 2:10 pm
    ORD Chicago
    1h 21m

    Return: Chicago to Cleveland

    ORD
    7:30 am
    1h 18m
    CLE
    9:48 am
    Airlines
    Flight No.
    From
    To
    Duration
    UA410
    Sun 14 Sep, 7:30 am
    ORD Chicago
    Sun 14 Sep, 9:48 am
    CLE Cleveland
    1h 18m
    Depart:Fri, 12 Sep Return:Sun, 14 Sep Cleveland to Chicago Fri, 12 Sep - Sun, 14 Sep
    United Airlines Direct 1h 23m
    6:00 am CLE - 6:23 am ORD
    United Airlines Direct 1h 17m
    9:55 pm ORD - 12:12 am (+1) CLE
    US$236
    united.com
    Show Details

    Depart: Cleveland to Chicago

    CLE
    6:00 am
    1h 23m
    ORD
    6:23 am
    Airlines
    Flight No.
    From
    To
    Duration
    UA3520
    Fri 12 Sep, 6:00 am
    CLE Cleveland
    Fri 12 Sep, 6:23 am
    ORD Chicago
    1h 23m

    Return: Chicago to Cleveland

    ORD
    9:55 pm
    1h 17m
    CLE
    12:12 am (+1)
    Airlines
    Flight No.
    From
    To
    Duration
    UA230
    Sun 14 Sep, 9:55 pm
    ORD Chicago
    Mon 15 Sep, 12:12 am
    CLE Cleveland
    1h 17m
    Depart:Thu, 20 Nov Return:Wed, 26 Nov New York to Chicago Thu, 20 Nov - Wed, 26 Nov
    Southwest Airlines Direct 2h 25m
    6:05 am EWR - 7:30 am MDW
    Southwest Airlines Direct 2h
    6:00 am MDW - 9:00 am EWR
    US$256
    fly.co.uk
    Show Details

    Depart: New York to Chicago

    EWR
    6:05 am
    2h 25m
    MDW
    7:30 am
    Airlines
    Flight No.
    From
    To
    Duration
    WN153
    Thu 20 Nov, 6:05 am
    EWR New York
    Thu 20 Nov, 7:30 am
    MDW Chicago
    2h 25m

    Return: Chicago to New York

    MDW
    6:00 am
    2h
    EWR
    9:00 am
    Airlines
    Flight No.
    From
    To
    Duration
    WN2868
    Wed 26 Nov, 6:00 am
    MDW Chicago
    Wed 26 Nov, 9:00 am
    EWR New York
    2h
    Depart:Thu, 20 Nov Return:Wed, 26 Nov New York to Chicago Thu, 20 Nov - Wed, 26 Nov
    Southwest Airlines Direct 2h 25m
    4:30 pm EWR - 5:55 pm MDW
    Southwest Airlines Direct 2h
    6:00 am MDW - 9:00 am EWR
    US$256
    fly.co.uk
    Show Details

    Depart: New York to Chicago

    EWR
    4:30 pm
    2h 25m
    MDW
    5:55 pm
    Airlines
    Flight No.
    From
    To
    Duration
    WN4883
    Thu 20 Nov, 4:30 pm
    EWR New York
    Thu 20 Nov, 5:55 pm
    MDW Chicago
    2h 25m

    Return: Chicago to New York

    MDW
    6:00 am
    2h
    EWR
    9:00 am
    Airlines
    Flight No.
    From
    To
    Duration
    WN2868
    Wed 26 Nov, 6:00 am
    MDW Chicago
    Wed 26 Nov, 9:00 am
    EWR New York
    2h
    Depart:Thu, 20 Nov Return:Wed, 26 Nov New York to Chicago Thu, 20 Nov - Wed, 26 Nov
    Delta Air Lines Direct 2h 42m
    6:15 am LGA - 7:57 am ORD
    Delta Air Lines Direct 2h 9m
    7:30 am ORD - 10:39 am LGA
    US$273
    us.bravofly.com
    Show Details

    Depart: New York to Chicago

    LGA
    6:15 am
    2h 42m
    ORD
    7:57 am
    Airlines
    Flight No.
    From
    To
    Duration
    DL5931
    Thu 20 Nov, 6:15 am
    LGA New York
    Thu 20 Nov, 7:57 am
    ORD Chicago
    2h 42m

    Return: Chicago to New York

    ORD
    7:30 am
    2h 9m
    LGA
    10:39 am
    Airlines
    Flight No.
    From
    To
    Duration
    DL5934
    Wed 26 Nov, 7:30 am
    ORD Chicago
    Wed 26 Nov, 10:39 am
    LGA New York
    2h 9m
    Depart:Thu, 20 Nov Return:Wed, 26 Nov New York to Chicago Thu, 20 Nov - Wed, 26 Nov
    Delta Air Lines Direct 2h 45m
    5:15 pm LGA - 7:00 pm ORD
    Delta Air Lines Direct 2h 9m
    7:30 am ORD - 10:39 am LGA
    US$273
    us.bravofly.com
    Show Details

    Depart: New York to Chicago

    LGA
    5:15 pm
    2h 45m
    ORD
    7:00 pm
    Airlines
    Flight No.
    From
    To
    Duration
    DL5953
    Thu 20 Nov, 5:15 pm
    LGA New York
    Thu 20 Nov, 7:00 pm
    ORD Chicago
    2h 45m

    Return: Chicago to New York

    ORD
    7:30 am
    2h 9m
    LGA
    10:39 am
    Airlines
    Flight No.
    From
    To
    Duration
    DL5934
    Wed 26 Nov, 7:30 am
    ORD Chicago
    Wed 26 Nov, 10:39 am
    LGA New York
    2h 9m
    Depart:Thu, 20 Nov Return:Wed, 26 Nov New York to Chicago Thu, 20 Nov - Wed, 26 Nov
    Delta Air Lines Direct 2h 42m
    6:15 am LGA - 7:57 am ORD
    Delta Air Lines Direct 2h 12m
    6:30 pm ORD - 9:42 pm LGA
    US$273
    us.bravofly.com
    Show Details

    Depart: New York to Chicago

    LGA
    6:15 am
    2h 42m
    ORD
    7:57 am
    Airlines
    Flight No.
    From
    To
    Duration
    DL5931
    Thu 20 Nov, 6:15 am
    LGA New York
    Thu 20 Nov, 7:57 am
    ORD Chicago
    2h 42m

    Return: Chicago to New York

    ORD
    6:30 pm
    2h 12m
    LGA
    9:42 pm
    Airlines
    Flight No.
    From
    To
    Duration
    DL5956
    Wed 26 Nov, 6:30 pm
    ORD Chicago
    Wed 26 Nov, 9:42 pm
    LGA New York
    2h 12m
    Depart:Thu, 20 Nov Return:Wed, 26 Nov New York to Chicago Thu, 20 Nov - Wed, 26 Nov
    Delta Air Lines Direct 2h 49m
    8:15 am JFK - 10:04 am ORD
    Delta Air Lines Direct 2h 12m
    6:30 pm ORD - 9:42 pm LGA
    US$273
    us.bravofly.com
    Show Details

    Depart: New York to Chicago

    JFK
    8:15 am
    2h 49m
    ORD
    10:04 am
    Airlines
    Flight No.
    From
    To
    Duration
    DL2926
    Thu 20 Nov, 8:15 am
    JFK New York
    Thu 20 Nov, 10:04 am
    ORD Chicago
    2h 49m

    Return: Chicago to New York

    ORD
    6:30 pm
    2h 12m
    LGA
    9:42 pm
    Airlines
    Flight No.
    From
    To
    Duration
    DL5956
    Wed 26 Nov, 6:30 pm
    ORD Chicago
    Wed 26 Nov, 9:42 pm
    LGA New York
    2h 12m
    Depart:Thu, 20 Nov Return:Wed, 26 Nov New York to Chicago Thu, 20 Nov - Wed, 26 Nov
    Delta Air Lines Direct 2h 49m
    8:15 am JFK - 10:04 am ORD
    Delta Air Lines Direct 2h 9m
    7:30 am ORD - 10:39 am LGA
    US$273
    us.bravofly.com
    Show Details

    Depart: New York to Chicago

    JFK
    8:15 am
    2h 49m
    ORD
    10:04 am
    Airlines
    Flight No.
    From
    To
    Duration
    DL2926
    Thu 20 Nov, 8:15 am
    JFK New York
    Thu 20 Nov, 10:04 am
    ORD Chicago
    2h 49m

    Return: Chicago to New York

    ORD
    7:30 am
    2h 9m
    LGA
    10:39 am
    Airlines
    Flight No.
    From
    To
    Duration
    DL5934
    Wed 26 Nov, 7:30 am
    ORD Chicago
    Wed 26 Nov, 10:39 am
    LGA New York
    2h 9m
    Depart:Thu, 20 Nov Return:Wed, 26 Nov New York to Chicago Thu, 20 Nov - Wed, 26 Nov
    Spirit Airlines Direct 2h 36m
    8:30 am LGA - 10:06 am ORD
    Spirit Airlines Direct 2h 9m
    5:56 pm ORD - 9:05 pm LGA
    US$274
    onetravel.com
    Show Details

    Depart: New York to Chicago

    LGA
    8:30 am
    2h 36m
    ORD
    10:06 am
    Airlines
    Flight No.
    From
    To
    Duration
    NK847
    Thu 20 Nov, 8:30 am
    LGA New York
    Thu 20 Nov, 10:06 am
    ORD Chicago
    2h 36m

    Return: Chicago to New York

    ORD
    5:56 pm
    2h 9m
    LGA
    9:05 pm
    Airlines
    Flight No.
    From
    To
    Duration
    NK630
    Wed 26 Nov, 5:56 pm
    ORD Chicago
    Wed 26 Nov, 9:05 pm
    LGA New York
    2h 9m
    Depart:Thu, 20 Nov Return:Wed, 26 Nov New York to Chicago Thu, 20 Nov - Wed, 26 Nov
    Southwest Airlines Direct 2h 35m
    6:00 pm EWR - 7:35 pm MDW
    Southwest Airlines Direct 2h
    6:00 am MDW - 9:00 am EWR
    US$276
    skypicker.com
    Show Details

    Depart: New York to Chicago

    EWR
    6:00 pm
    2h 35m
    MDW
    7:35 pm
    Airlines
    Flight No.
    From
    To
    Duration
    WN342
    Thu 20 Nov, 6:00 pm
    EWR New York
    Thu 20 Nov, 7:35 pm
    MDW Chicago
    2h 35m

    Return: Chicago to New York

    MDW
    6:00 am
    2h
    EWR
    9:00 am
    Airlines
    Flight No.
    From
    To
    Duration
    WN2868
    Wed 26 Nov, 6:00 am
    MDW Chicago
    Wed 26 Nov, 9:00 am
    EWR New York
    2h
    Depart:Thu, 20 Nov Return:Wed, 26 Nov New York to Chicago Thu, 20 Nov - Wed, 26 Nov
    Spirit Airlines Direct 2h 23m
    9:55 pm LGA - 11:18 pm ORD
    Southwest Airlines Direct 2h
    8:35 am MDW - 11:35 am EWR
    US$276
    fly.co.uk
    Show Details

    Depart: New York to Chicago

    LGA
    9:55 pm
    2h 23m
    ORD
    11:18 pm
    Airlines
    Flight No.
    From
    To
    Duration
    NK331
    Thu 20 Nov, 9:55 pm
    LGA New York
    Thu 20 Nov, 11:18 pm
    ORD Chicago
    2h 23m

    Return: Chicago to New York

    MDW
    8:35 am
    2h
    EWR
    11:35 am
    Airlines
    Flight No.
    From
    To
    Duration
    WN136
    Wed 26 Nov, 8:35 am
    MDW Chicago
    Wed 26 Nov, 11:35 am
    EWR New York
    2h