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1. www.southwest.com › routes › flights-from-boston-to-chicagoFlights from Boston Logan to Chicago (Midway) | Southwest...

   www.southwest.com › routes › flights-from-boston-to-chicago

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   Book flights from Boston Logan to Chicago (Midway) with Southwest Airlines®. Bundle your flight with a hotel or rental car booking and find even more savings.

2. www.kayak.com › flight-routes › Boston-Logan-Intl-BOS$26 Cheap Flights from Boston to Chicago (BOS - CHI) | KAYAK

   www.kayak.com › flight-routes › Boston-Logan-Intl-BOS

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   Our data shows that the cheapest route for a one-way flight from Boston to Chicago cost $68 and was between Boston and Chicago O'Hare Intl Airport. On average, the best prices are found if you fly from Boston to Chicago Midway Airport. The average price for a return flight for this route is $86.

3. www.kayak.com › flight-routes › Boston-Logan-Intl-BOS$74 Cheap Flights from Boston to Chicago Midway (BOS - KAYAK

   www.kayak.com › flight-routes › Boston-Logan-Intl-BOS

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   The cheapest return flight ticket from Boston to Chicago Midway Airport found by KAYAK users in the last 72 hours was for $99 on Frontier, followed by Southwest ($191). One-way flight deals have also been found from as low as $74 on Frontier and from $104 on Southwest.

4. www.google.com › travel › flightsFind Cheap Flights from Boston to Chicago - Google Flights

   www.google.com › travel › flights

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   Flights from Boston to Chicago. Use Google Flights to plan your next trip and find cheap one way or round trip flights from Boston to Chicago. Find the best flights fast,...

5. www.southwest.com › destinations › midwestFlights to Chicago (Midway) | Southwest Airlines®

   www.southwest.com › destinations › midwest

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   Visit the Windy City with nonstop flights to Chicago (Midway) on Southwest Airlines®. Whether business or vacation, don't overpay for your next trip.

6. www.skyscanner.net › routes › bosaCheap Flights from Boston to Chicago - Skyscanner

   www.skyscanner.net › routes › bosa

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   Compare cheap flights and find tickets from Boston (BOS) to Chicago (CHI). Book directly with no added fees.

7. cheapflightsplus.com › airline › southwest-airlinesSouthwest Airlines Boston to Chicago Flights - Cheap flight...

   cheapflightsplus.com › airline › southwest-airlines

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   Cheap Flights from Boston to Chicago by Southwest Airlines. Look at the list of plane tickets for the most popular direct and connecting flights by Southwest Airlines, their prices start from $127. The fastest nonstop flight takes 2h 45m. The fastest connecting flight — 4h 25m.