Cheap Flights to Chicago
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    Cheap Flights to Chicago

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    Spirit Airlines 22 results US$101 View Flights
    Frontier Airlines 2 results US$199 View Flights
    United Airlines 175 results US$247 View Flights
    American Airlines 236 results US$250 View Flights
    US Airways 82 results US$250 View Flights
    JetBlue Airways 20 results US$250 View Flights
    Southwest Airlines 32 results US$253 View Flights
    Delta Air Lines 16 results US$334 View Flights
    Virgin America 10 results US$649 View Flights
    Depart: Sat, 15 Nov Return: Sat, 22 Nov Minneapolis/St Paul to Chicago Sat, 15 Nov - Sat, 22 Nov
    Spirit Airlines Direct 1h 30m
    6:50 pm MSP - 8:20 pm ORD
    Spirit Airlines Direct 1h 26m
    7:48 pm ORD - 9:14 pm MSP
    US$101
    onetravel.com
    Show Details

    Depart: Minneapolis/St Paul to Chicago

    MSP
    6:50 pm
    1h 30m
    ORD
    8:20 pm
    Airlines
    Flight No.
    From
    To
    Duration
    NK614
    6:50 pm, 15 Nov Sat
    MSP Minneapolis/St Paul
    8:20 pm, 15 Nov Sat
    ORD Chicago
    1h 30m

    Return: Chicago to Minneapolis/St Paul

    ORD
    7:48 pm
    1h 26m
    MSP
    9:14 pm
    Airlines
    Flight No.
    From
    To
    Duration
    NK763
    7:48 pm, 22 Nov Sat
    ORD Chicago
    9:14 pm, 22 Nov Sat
    MSP Minneapolis/St Paul
    1h 26m
    Depart: Sat, 15 Nov Return: Sat, 22 Nov Minneapolis/St Paul to Chicago Sat, 15 Nov - Sat, 22 Nov
    Spirit Airlines Direct 1h 30m
    6:50 pm MSP - 8:20 pm ORD
    Spirit Airlines Direct 1h 25m
    9:05 am ORD - 10:30 am MSP
    US$101
    onetravel.com
    Show Details

    Depart: Minneapolis/St Paul to Chicago

    MSP
    6:50 pm
    1h 30m
    ORD
    8:20 pm
    Airlines
    Flight No.
    From
    To
    Duration
    NK614
    6:50 pm, 15 Nov Sat
    MSP Minneapolis/St Paul
    8:20 pm, 15 Nov Sat
    ORD Chicago
    1h 30m

    Return: Chicago to Minneapolis/St Paul

    ORD
    9:05 am
    1h 25m
    MSP
    10:30 am
    Airlines
    Flight No.
    From
    To
    Duration
    NK761
    9:05 am, 22 Nov Sat
    ORD Chicago
    10:30 am, 22 Nov Sat
    MSP Minneapolis/St Paul
    1h 25m
    Depart: Sat, 15 Nov Return: Sat, 22 Nov Minneapolis/St Paul to Chicago Sat, 15 Nov - Sat, 22 Nov
    Spirit Airlines Direct 1h 25m
    6:20 am MSP - 7:45 am ORD
    Spirit Airlines Direct 1h 26m
    7:48 pm ORD - 9:14 pm MSP
    US$111
    onetravel.com
    Show Details

    Depart: Minneapolis/St Paul to Chicago

    MSP
    6:20 am
    1h 25m
    ORD
    7:45 am
    Airlines
    Flight No.
    From
    To
    Duration
    NK612
    6:20 am, 15 Nov Sat
    MSP Minneapolis/St Paul
    7:45 am, 15 Nov Sat
    ORD Chicago
    1h 25m

    Return: Chicago to Minneapolis/St Paul

    ORD
    7:48 pm
    1h 26m
    MSP
    9:14 pm
    Airlines
    Flight No.
    From
    To
    Duration
    NK763
    7:48 pm, 22 Nov Sat
    ORD Chicago
    9:14 pm, 22 Nov Sat
    MSP Minneapolis/St Paul
    1h 26m
    Depart: Fri, 31 Oct Return: Sun, 2 Nov Boston to Chicago Fri, 31 Oct - Sun, 2 Nov
    Spirit Airlines Direct 2h 40m
    1:30 pm BOS - 3:10 pm ORD
    JetBlue Airways Direct 2h 12m
    6:00 am ORD - 9:12 am BOS
    US$151
    edreams.net
    Show Details

    Depart: Boston to Chicago

    BOS
    1:30 pm
    2h 40m
    ORD
    3:10 pm
    Airlines
    Flight No.
    From
    To
    Duration
    NK773
    1:30 pm, 31 Oct Fri
    BOS Boston
    3:10 pm, 31 Oct Fri
    ORD Chicago
    2h 40m

    Return: Chicago to Boston

    ORD
    6:00 am
    2h 12m
    BOS
    9:12 am
    Airlines
    Flight No.
    From
    To
    Duration
    B61012
    6:00 am, 2 Nov Sun
    ORD Chicago
    9:12 am, 2 Nov Sun
    BOS Boston
    2h 12m
    Depart: Fri, 31 Oct Return: Sun, 2 Nov Boston to Chicago Fri, 31 Oct - Sun, 2 Nov
    Spirit Airlines Direct 2h 40m
    1:30 pm BOS - 3:10 pm ORD
    United Airlines Direct 2h 18m
    8:45 am ORD - 12:03 pm BOS
    US$197
    edreams.net
    Show Details

    Depart: Boston to Chicago

    BOS
    1:30 pm
    2h 40m
    ORD
    3:10 pm
    Airlines
    Flight No.
    From
    To
    Duration
    NK773
    1:30 pm, 31 Oct Fri
    BOS Boston
    3:10 pm, 31 Oct Fri
    ORD Chicago
    2h 40m

    Return: Chicago to Boston

    ORD
    8:45 am
    2h 18m
    BOS
    12:03 pm
    Airlines
    Flight No.
    From
    To
    Duration
    UA1655
    8:45 am, 2 Nov Sun
    ORD Chicago
    12:03 pm, 2 Nov Sun
    BOS Boston
    2h 18m
    Depart: Fri, 31 Oct Return: Sun, 2 Nov Boston to Chicago Fri, 31 Oct - Sun, 2 Nov
    Spirit Airlines Direct 2h 40m
    1:30 pm BOS - 3:10 pm ORD
    US Airways Direct 2h 10m
    6:15 am ORD - 9:25 am BOS
    US$197
    edreams.net
    Show Details

    Depart: Boston to Chicago

    BOS
    1:30 pm
    2h 40m
    ORD
    3:10 pm
    Airlines
    Flight No.
    From
    To
    Duration
    NK773
    1:30 pm, 31 Oct Fri
    BOS Boston
    3:10 pm, 31 Oct Fri
    ORD Chicago
    2h 40m

    Return: Chicago to Boston

    ORD
    6:15 am
    2h 10m
    BOS
    9:25 am
    Airlines
    Flight No.
    From
    To
    Duration
    US26
    6:15 am, 2 Nov Sun
    ORD Chicago
    9:25 am, 2 Nov Sun
    BOS Boston
    2h 10m
    Depart: Fri, 31 Oct Return: Sun, 2 Nov Boston to Chicago Fri, 31 Oct - Sun, 2 Nov
    Spirit Airlines Direct 2h 40m
    1:30 pm BOS - 3:10 pm ORD
    US Airways Direct 2h 10m
    10:05 pm ORD - 1:15 am (+1) BOS
    US$197
    edreams.net
    Show Details

    Depart: Boston to Chicago

    BOS
    1:30 pm
    2h 40m
    ORD
    3:10 pm
    Airlines
    Flight No.
    From
    To
    Duration
    NK773
    1:30 pm, 31 Oct Fri
    BOS Boston
    3:10 pm, 31 Oct Fri
    ORD Chicago
    2h 40m

    Return: Chicago to Boston

    ORD
    10:05 pm
    2h 10m
    BOS
    1:15 am (+1)
    Airlines
    Flight No.
    From
    To
    Duration
    US2221
    10:05 pm, 2 Nov Sun
    ORD Chicago
    1:15 am, 3 Nov Mon
    BOS Boston
    2h 10m
    Depart: Fri, 31 Oct Return: Sun, 2 Nov Boston to Chicago Fri, 31 Oct - Sun, 2 Nov
    Spirit Airlines Direct 2h 40m
    1:30 pm BOS - 3:10 pm ORD
    US Airways Direct 2h 10m
    8:10 am ORD - 11:20 am BOS
    US$197
    edreams.net
    Show Details

    Depart: Boston to Chicago

    BOS
    1:30 pm
    2h 40m
    ORD
    3:10 pm
    Airlines
    Flight No.
    From
    To
    Duration
    NK773
    1:30 pm, 31 Oct Fri
    BOS Boston
    3:10 pm, 31 Oct Fri
    ORD Chicago
    2h 40m

    Return: Chicago to Boston

    ORD
    8:10 am
    2h 10m
    BOS
    11:20 am
    Airlines
    Flight No.
    From
    To
    Duration
    US1551
    8:10 am, 2 Nov Sun
    ORD Chicago
    11:20 am, 2 Nov Sun
    BOS Boston
    2h 10m
    Depart: Fri, 31 Oct Return: Sun, 2 Nov Boston to Chicago Fri, 31 Oct - Sun, 2 Nov
    Spirit Airlines Direct 2h 40m
    1:30 pm BOS - 3:10 pm ORD
    United Airlines Direct 2h 15m
    10:27 am ORD - 1:42 pm BOS
    US$197
    edreams.net
    Show Details

    Depart: Boston to Chicago

    BOS
    1:30 pm
    2h 40m
    ORD
    3:10 pm
    Airlines
    Flight No.
    From
    To
    Duration
    NK773
    1:30 pm, 31 Oct Fri
    BOS Boston
    3:10 pm, 31 Oct Fri
    ORD Chicago
    2h 40m

    Return: Chicago to Boston

    ORD
    10:27 am
    2h 15m
    BOS
    1:42 pm
    Airlines
    Flight No.
    From
    To
    Duration
    UA1547
    10:27 am, 2 Nov Sun
    ORD Chicago
    1:42 pm, 2 Nov Sun
    BOS Boston
    2h 15m
    Depart: Fri, 31 Oct Return: Sun, 2 Nov Boston to Chicago Fri, 31 Oct - Sun, 2 Nov
    Spirit Airlines Direct 2h 40m
    1:30 pm BOS - 3:10 pm ORD
    United Airlines Direct 2h 18m
    9:19 pm ORD - 12:37 am (+1) BOS
    US$197
    edreams.net
    Show Details

    Depart: Boston to Chicago

    BOS
    1:30 pm
    2h 40m
    ORD
    3:10 pm
    Airlines
    Flight No.
    From
    To
    Duration
    NK773
    1:30 pm, 31 Oct Fri
    BOS Boston
    3:10 pm, 31 Oct Fri
    ORD Chicago
    2h 40m

    Return: Chicago to Boston

    ORD
    9:19 pm
    2h 18m
    BOS
    12:37 am (+1)
    Airlines
    Flight No.
    From
    To
    Duration
    UA578
    9:19 pm, 2 Nov Sun
    ORD Chicago
    12:37 am, 3 Nov Mon
    BOS Boston
    2h 18m
    Depart: Fri, 14 Nov Return: Sun, 16 Nov Phoenix to Chicago Fri, 14 Nov - Sun, 16 Nov
    Frontier Airlines Direct 3h 20m
    10:30 am PHX - 2:50 pm ORD
    Frontier Airlines Direct 3h 45m
    7:00 am ORD - 9:45 am PHX
    US$199
    expedia.com
    Show Details

    Depart: Phoenix to Chicago

    PHX
    10:30 am
    3h 20m
    ORD
    2:50 pm
    Airlines
    Flight No.
    From
    To
    Duration
    F91060
    10:30 am, 14 Nov Fri
    PHX Phoenix
    2:50 pm, 14 Nov Fri
    ORD Chicago
    3h 20m

    Return: Chicago to Phoenix

    ORD
    7:00 am
    3h 45m
    PHX
    9:45 am
    Airlines
    Flight No.
    From
    To
    Duration
    F91061
    7:00 am, 16 Nov Sun
    ORD Chicago
    9:45 am, 16 Nov Sun
    PHX Phoenix
    3h 45m
    Depart: Fri, 31 Oct Return: Sun, 2 Nov Boston to Chicago Fri, 31 Oct - Sun, 2 Nov
    Spirit Airlines Direct 2h 40m
    1:30 pm BOS - 3:10 pm ORD
    United Airlines Direct 2h 14m
    11:00 am ORD - 2:14 pm BOS
    US$225
    edreams.net
    Show Details

    Depart: Boston to Chicago

    BOS
    1:30 pm
    2h 40m
    ORD
    3:10 pm
    Airlines
    Flight No.
    From
    To
    Duration
    NK773
    1:30 pm, 31 Oct Fri
    BOS Boston
    3:10 pm, 31 Oct Fri
    ORD Chicago
    2h 40m

    Return: Chicago to Boston

    ORD
    11:00 am
    2h 14m
    BOS
    2:14 pm
    Airlines
    Flight No.
    From
    To
    Duration
    UA5204
    11:00 am, 2 Nov Sun
    ORD Chicago
    2:14 pm, 2 Nov Sun
    BOS Boston
    2h 14m
    Depart: Tue, 4 Nov Return: Fri, 7 Nov New York to Chicago Tue, 4 Nov - Fri, 7 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$226
    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
    8:30 am, 4 Nov Tue
    LGA New York
    10:06 am, 4 Nov Tue
    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
    5:56 pm, 7 Nov Fri
    ORD Chicago
    9:05 pm, 7 Nov Fri
    LGA New York
    2h 9m
    Depart: Sun, 2 Nov Return: Wed, 5 Nov New York to Chicago Sun, 2 Nov - Wed, 5 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$226
    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
    8:30 am, 2 Nov Sun
    LGA New York
    10:06 am, 2 Nov Sun
    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
    5:56 pm, 5 Nov Wed
    ORD Chicago
    9:05 pm, 5 Nov Wed
    LGA New York
    2h 9m
    Depart: Thu, 20 Nov Return: Wed, 26 Nov New York to Chicago Thu, 20 Nov - Wed, 26 Nov
    United Airlines Direct 2h 31m
    1:50 pm EWR - 3:21 pm ORD
    Delta Air Lines Direct 2h 7m
    8:00 am ORD - 11:07 am JFK
    US$247
    us.bravofly.com
    Show Details

    Depart: New York to Chicago

    EWR
    1:50 pm
    2h 31m
    ORD
    3:21 pm
    Airlines
    Flight No.
    From
    To
    Duration
    UA224
    1:50 pm, 20 Nov Thu
    EWR New York
    3:21 pm, 20 Nov Thu
    ORD Chicago
    2h 31m

    Return: Chicago to New York

    ORD
    8:00 am
    2h 7m
    JFK
    11:07 am
    Airlines
    Flight No.
    From
    To
    Duration
    DL3323
    8:00 am, 26 Nov Wed
    ORD Chicago
    11:07 am, 26 Nov Wed
    JFK New York
    2h 7m
    Depart: Thu, 20 Nov Return: Wed, 26 Nov New York to Chicago Thu, 20 Nov - Wed, 26 Nov
    United Airlines Direct 2h 31m
    1:50 pm EWR - 3:21 pm ORD
    American Airlines Direct 2h
    6:35 am ORD - 9:35 am LGA
    US$249
    airtickets.com
    Show Details

    Depart: New York to Chicago

    EWR
    1:50 pm
    2h 31m
    ORD
    3:21 pm
    Airlines
    Flight No.
    From
    To
    Duration
    UA224
    1:50 pm, 20 Nov Thu
    EWR New York
    3:21 pm, 20 Nov Thu
    ORD Chicago
    2h 31m

    Return: Chicago to New York

    ORD
    6:35 am
    2h
    LGA
    9:35 am
    Airlines
    Flight No.
    From
    To
    Duration
    AA394
    6:35 am, 26 Nov Wed
    ORD Chicago
    9:35 am, 26 Nov Wed
    LGA New York
    2h
    Depart: Thu, 20 Nov Return: Wed, 26 Nov New York to Chicago Thu, 20 Nov - Wed, 26 Nov
    United Airlines Direct 2h 31m
    1:50 pm EWR - 3:21 pm ORD
    American Airlines Direct 2h
    5:00 pm ORD - 8:00 pm LGA
    US$249
    airtickets.com
    Show Details

    Depart: New York to Chicago

    EWR
    1:50 pm
    2h 31m
    ORD
    3:21 pm
    Airlines
    Flight No.
    From
    To
    Duration
    UA224
    1:50 pm, 20 Nov Thu
    EWR New York
    3:21 pm, 20 Nov Thu
    ORD Chicago
    2h 31m

    Return: Chicago to New York

    ORD
    5:00 pm
    2h
    LGA
    8:00 pm
    Airlines
    Flight No.
    From
    To
    Duration
    AA354
    5:00 pm, 26 Nov Wed
    ORD Chicago
    8:00 pm, 26 Nov Wed
    LGA New York
    2h
    Depart: Fri, 31 Oct Return: Sun, 2 Nov Boston to Chicago Fri, 31 Oct - Sun, 2 Nov
    American Airlines Direct 2h 45m
    2:00 pm BOS - 3:45 pm ORD
    JetBlue Airways Direct 2h 12m
    6:00 am ORD - 9:12 am BOS
    US$250
    us.bravofly.com
    Show Details

    Depart: Boston to Chicago

    BOS
    2:00 pm
    2h 45m
    ORD
    3:45 pm
    Airlines
    Flight No.
    From
    To
    Duration
    AA187
    2:00 pm, 31 Oct Fri
    BOS Boston
    3:45 pm, 31 Oct Fri
    ORD Chicago
    2h 45m

    Return: Chicago to Boston

    ORD
    6:00 am
    2h 12m
    BOS
    9:12 am
    Airlines
    Flight No.
    From
    To
    Duration
    B61012
    6:00 am, 2 Nov Sun
    ORD Chicago
    9:12 am, 2 Nov Sun
    BOS Boston
    2h 12m
    Depart: Fri, 31 Oct Return: Sun, 2 Nov Boston to Chicago Fri, 31 Oct - Sun, 2 Nov
    US Airways Direct 2h 40m
    12:05 pm BOS - 1:45 pm ORD
    JetBlue Airways Direct 2h 12m
    6:00 am ORD - 9:12 am BOS
    US$250
    us.bravofly.com
    Show Details

    Depart: Boston to Chicago

    BOS
    12:05 pm
    2h 40m
    ORD
    1:45 pm
    Airlines
    Flight No.
    From
    To
    Duration
    US1551
    12:05 pm, 31 Oct Fri
    BOS Boston
    1:45 pm, 31 Oct Fri
    ORD Chicago
    2h 40m

    Return: Chicago to Boston

    ORD
    6:00 am
    2h 12m
    BOS
    9:12 am
    Airlines
    Flight No.
    From
    To
    Duration
    B61012
    6:00 am, 2 Nov Sun
    ORD Chicago
    9:12 am, 2 Nov Sun
    BOS Boston
    2h 12m
    Depart: Fri, 31 Oct Return: Sun, 2 Nov Boston to Chicago Fri, 31 Oct - Sun, 2 Nov
    American Airlines Direct 2h 50m
    7:10 am BOS - 9:00 am ORD
    JetBlue Airways Direct 2h 12m
    6:00 am ORD - 9:12 am BOS
    US$250
    us.bravofly.com
    Show Details

    Depart: Boston to Chicago

    BOS
    7:10 am
    2h 50m
    ORD
    9:00 am
    Airlines
    Flight No.
    From
    To
    Duration
    AA1247
    7:10 am, 31 Oct Fri
    BOS Boston
    9:00 am, 31 Oct Fri
    ORD Chicago
    2h 50m

    Return: Chicago to Boston

    ORD
    6:00 am
    2h 12m
    BOS
    9:12 am
    Airlines
    Flight No.
    From
    To
    Duration
    B61012
    6:00 am, 2 Nov Sun
    ORD Chicago
    9:12 am, 2 Nov Sun
    BOS Boston
    2h 12m