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    Cheap Flights to Chicago

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    Frontier Airlines 4 results US$194 View Flights
    United Airlines 702 results US$236 View Flights
    Southwest Airlines 87 results US$246 View Flights
    American Airlines 490 results US$258 View Flights
    Delta Air Lines 94 results US$271 View Flights
    Spirit Airlines 6 results US$274 View Flights
    US Airways 109 results US$292 View Flights
    JetBlue Airways 1 result US$371 View Flights
    Virgin America 3 results US$453 View Flights
    Alaska Airlines 134 results US$495 View Flights
    Depart:Thu, 9 Oct Return:Mon, 13 Oct Washington to Chicago Thu, 9 Oct - Mon, 13 Oct
    Frontier Airlines Direct 1h 55m
    5:30 pm IAD - 6:25 pm ORD
    Frontier Airlines Direct 1h 45m
    8:35 am ORD - 11:20 am IAD
    US$194
    onetravel.com
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    Depart: Washington to Chicago

    IAD
    5:30 pm
    1h 55m
    ORD
    6:25 pm
    Airlines
    Flight No.
    From
    To
    Duration
    F91344
    Thu 9 Oct, 5:30 pm
    IAD Washington
    Thu 9 Oct, 6:25 pm
    ORD Chicago
    1h 55m

    Return: Chicago to Washington

    ORD
    8:35 am
    1h 45m
    IAD
    11:20 am
    Airlines
    Flight No.
    From
    To
    Duration
    F91343
    Mon 13 Oct, 8:35 am
    ORD Chicago
    Mon 13 Oct, 11:20 am
    IAD Washington
    1h 45m
    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
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    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
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    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$246
    fly.co.uk
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    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$255
    fly.co.uk
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    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:Sat, 20 Sep Return:Sun, 21 Sep Washington to Chicago Sat, 20 Sep - Sun, 21 Sep
    American Airlines Direct 2h 5m
    9:59 am DCA - 11:04 am ORD
    American Airlines Direct 1h 45m
    6:15 am ORD - 9:00 am DCA
    US$258
    airtickets.com
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    Depart: Washington to Chicago

    DCA
    9:59 am
    2h 5m
    ORD
    11:04 am
    Airlines
    Flight No.
    From
    To
    Duration
    AA40
    Sat 20 Sep, 9:59 am
    DCA Washington
    Sat 20 Sep, 11:04 am
    ORD Chicago
    2h 5m

    Return: Chicago to Washington

    ORD
    6:15 am
    1h 45m
    DCA
    9:00 am
    Airlines
    Flight No.
    From
    To
    Duration
    AA40
    Sun 21 Sep, 6:15 am
    ORD Chicago
    Sun 21 Sep, 9:00 am
    DCA Washington
    1h 45m
    Depart:Sat, 20 Sep Return:Sun, 21 Sep Washington to Chicago Sat, 20 Sep - Sun, 21 Sep
    American Airlines Direct 2h 6m
    7:05 pm DCA - 8:11 pm ORD
    American Airlines Direct 1h 45m
    6:15 am ORD - 9:00 am DCA
    US$258
    airtickets.com
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    Depart: Washington to Chicago

    DCA
    7:05 pm
    2h 6m
    ORD
    8:11 pm
    Airlines
    Flight No.
    From
    To
    Duration
    AA4259
    Sat 20 Sep, 7:05 pm
    DCA Washington
    Sat 20 Sep, 8:11 pm
    ORD Chicago
    2h 6m

    Return: Chicago to Washington

    ORD
    6:15 am
    1h 45m
    DCA
    9:00 am
    Airlines
    Flight No.
    From
    To
    Duration
    AA40
    Sun 21 Sep, 6:15 am
    ORD Chicago
    Sun 21 Sep, 9:00 am
    DCA Washington
    1h 45m
    Depart:Sat, 20 Sep Return:Sun, 21 Sep Washington to Chicago Sat, 20 Sep - Sun, 21 Sep
    American Airlines Direct 2h 5m
    1:50 pm DCA - 2:55 pm ORD
    American Airlines Direct 1h 45m
    6:15 am ORD - 9:00 am DCA
    US$258
    airtickets.com
    Show Details

    Depart: Washington to Chicago

    DCA
    1:50 pm
    2h 5m
    ORD
    2:55 pm
    Airlines
    Flight No.
    From
    To
    Duration
    AA1452
    Sat 20 Sep, 1:50 pm
    DCA Washington
    Sat 20 Sep, 2:55 pm
    ORD Chicago
    2h 5m

    Return: Chicago to Washington

    ORD
    6:15 am
    1h 45m
    DCA
    9:00 am
    Airlines
    Flight No.
    From
    To
    Duration
    AA40
    Sun 21 Sep, 6:15 am
    ORD Chicago
    Sun 21 Sep, 9:00 am
    DCA Washington
    1h 45m
    Depart:Sat, 20 Sep Return:Sun, 21 Sep Washington to Chicago Sat, 20 Sep - Sun, 21 Sep
    American Airlines Direct 2h 5m
    3:05 pm DCA - 4:10 pm ORD
    American Airlines Direct 1h 45m
    6:15 am ORD - 9:00 am DCA
    US$258
    airtickets.com
    Show Details

    Depart: Washington to Chicago

    DCA
    3:05 pm
    2h 5m
    ORD
    4:10 pm
    Airlines
    Flight No.
    From
    To
    Duration
    AA322
    Sat 20 Sep, 3:05 pm
    DCA Washington
    Sat 20 Sep, 4:10 pm
    ORD Chicago
    2h 5m

    Return: Chicago to Washington

    ORD
    6:15 am
    1h 45m
    DCA
    9:00 am
    Airlines
    Flight No.
    From
    To
    Duration
    AA40
    Sun 21 Sep, 6:15 am
    ORD Chicago
    Sun 21 Sep, 9:00 am
    DCA Washington
    1h 45m
    Depart:Sat, 20 Sep Return:Sun, 21 Sep Washington to Chicago Sat, 20 Sep - Sun, 21 Sep
    American Airlines Direct 2h 10m
    4:05 pm DCA - 5:15 pm ORD
    American Airlines Direct 1h 45m
    6:15 am ORD - 9:00 am DCA
    US$258
    airtickets.com
    Show Details

    Depart: Washington to Chicago

    DCA
    4:05 pm
    2h 10m
    ORD
    5:15 pm
    Airlines
    Flight No.
    From
    To
    Duration
    AA2407
    Sat 20 Sep, 4:05 pm
    DCA Washington
    Sat 20 Sep, 5:15 pm
    ORD Chicago
    2h 10m

    Return: Chicago to Washington

    ORD
    6:15 am
    1h 45m
    DCA
    9:00 am
    Airlines
    Flight No.
    From
    To
    Duration
    AA40
    Sun 21 Sep, 6:15 am
    ORD Chicago
    Sun 21 Sep, 9:00 am
    DCA Washington
    1h 45m
    Depart:Sat, 20 Sep Return:Sun, 21 Sep Washington to Chicago Sat, 20 Sep - Sun, 21 Sep
    American Airlines Direct 2h 5m
    6:05 am DCA - 7:10 am ORD
    American Airlines Direct 1h 45m
    6:15 am ORD - 9:00 am DCA
    US$258
    airtickets.com
    Show Details

    Depart: Washington to Chicago

    DCA
    6:05 am
    2h 5m
    ORD
    7:10 am
    Airlines
    Flight No.
    From
    To
    Duration
    AA1175
    Sat 20 Sep, 6:05 am
    DCA Washington
    Sat 20 Sep, 7:10 am
    ORD Chicago
    2h 5m

    Return: Chicago to Washington

    ORD
    6:15 am
    1h 45m
    DCA
    9:00 am
    Airlines
    Flight No.
    From
    To
    Duration
    AA40
    Sun 21 Sep, 6:15 am
    ORD Chicago
    Sun 21 Sep, 9:00 am
    DCA Washington
    1h 45m
    Depart:Sat, 20 Sep Return:Sun, 21 Sep Washington to Chicago Sat, 20 Sep - Sun, 21 Sep
    American Airlines Direct 2h 10m
    8:35 am DCA - 9:45 am ORD
    American Airlines Direct 1h 45m
    6:15 am ORD - 9:00 am DCA
    US$258
    airtickets.com
    Show Details

    Depart: Washington to Chicago

    DCA
    8:35 am
    2h 10m
    ORD
    9:45 am
    Airlines
    Flight No.
    From
    To
    Duration
    AA1409
    Sat 20 Sep, 8:35 am
    DCA Washington
    Sat 20 Sep, 9:45 am
    ORD Chicago
    2h 10m

    Return: Chicago to Washington

    ORD
    6:15 am
    1h 45m
    DCA
    9:00 am
    Airlines
    Flight No.
    From
    To
    Duration
    AA40
    Sun 21 Sep, 6:15 am
    ORD Chicago
    Sun 21 Sep, 9:00 am
    DCA Washington
    1h 45m
    Depart:Fri, 19 Sep Return:Sun, 21 Sep Washington to Chicago Fri, 19 Sep - Sun, 21 Sep
    American Airlines Direct 2h 5m
    6:05 am DCA - 7:10 am ORD
    American Airlines Direct 1h 45m
    6:15 am ORD - 9:00 am DCA
    US$258
    airtickets.com
    Show Details

    Depart: Washington to Chicago

    DCA
    6:05 am
    2h 5m
    ORD
    7:10 am
    Airlines
    Flight No.
    From
    To
    Duration
    AA1175
    Fri 19 Sep, 6:05 am
    DCA Washington
    Fri 19 Sep, 7:10 am
    ORD Chicago
    2h 5m

    Return: Chicago to Washington

    ORD
    6:15 am
    1h 45m
    DCA
    9:00 am
    Airlines
    Flight No.
    From
    To
    Duration
    AA40
    Sun 21 Sep, 6:15 am
    ORD Chicago
    Sun 21 Sep, 9:00 am
    DCA Washington
    1h 45m