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    Book with confidence - We have plenty of flexible travel options to choose from in case you need to change your plans.

    Cheap flight offers from Nashville to Chicago with Southwest Airlines

    COVID-19 updates. - For information on refunds and cancellations. To change your booking on My bravofly.com. Read up on the latest travel restrictions.

    Nashville to Chicago flights - Low cost deals with Southwest Airlines

    Nashville - Chicago

    Mon 1/25/21 Tue 1/26/21 Wed 1/27/21 Thu 1/28/21 Fri 1/29/21 Sat 1/30/21 Sun 1/31/21
    Mon 1/25/21
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    Nashville - Chicago Midway

    Mon 1/25/21 Tue 1/26/21 Wed 1/27/21 Thu 1/28/21 Fri 1/29/21 Sat 1/30/21 Sun 1/31/21
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    New York - Chicago

    Mon 1/25/21 Tue 1/26/21 Wed 1/27/21 Thu 1/28/21 Fri 1/29/21 Sat 1/30/21 Sun 1/31/21
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    Los Angeles - Chicago

    Mon 1/25/21 Tue 1/26/21 Wed 1/27/21 Thu 1/28/21 Fri 1/29/21 Sat 1/30/21 Sun 1/31/21
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    Prices refer to lowest available return flight, and are per person for the dates shown. The flights are subject to seat availability as well as variations in the price and tariffs.