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1. www.kayak.com › flight-routes › Chicago-CHI$32 Cheap Flights from Chicago to Boston (CHI - BOS) | KAYAK

   www.kayak.com › flight-routes › Chicago-CHI

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   KAYAK compares all flights & prices from United Airlines, American Airlines, Expedia, Spirit Airlines & more for flights from Chicago to Boston. Flights from $32. Search for Chicago to Boston flights now to find the best deal | KAYAK.

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

   www.google.com › travel › flights

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

3. www.expedia.com › lp › flights$24 Cheap flights from Chicago to Boston (CHI to BOS) - Expedia

   www.expedia.com › lp › flights

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   Book one-way or return flights from Chicago to Boston with no change fee on selected flights. Earn your airline miles on top of our rewards! Get great 2024 flight deals from Chicago to Boston now!

4. www.skyscanner.com › routes › mdw$45 Flights from Chicago (MDW) to Boston (BOS) | Skyscanner

   www.skyscanner.com › routes › mdw

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   Which is the cheapest airline to fly with from Chicago Midway Airport to Boston Logan International? Currently, Frontier Airlines offers the cheapest flight tickets to Boston Logan International. When it comes to history and culture, Beantown is hard to beat.

5. www.skyscanner.net › routes › chiaCheap Flights from Chicago to Boston Logan International

   www.skyscanner.net › routes › chia

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   From British Airways to international carriers like Emirates, we compare all major airlines along with the most popular online travel agents to find the cheapest plane tickets from Chicago to Boston Logan International.

6. www.kayak.com › flight-routes › Illinois-USIL$29 Cheap Flights from Illinois to Boston | KAYAK

   www.kayak.com › flight-routes › Illinois-USIL

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   Find flights to Boston from $29. Fly from Illinois on Spirit Airlines, Frontier, American Airlines and more. Search for Boston flights on KAYAK now to find the best deal.

7. www.kayak.com › flight-routes › Chicago-Midway-MDW$50 Cheap Flights from Chicago Midway to Boston (MDW - KAYAK

   www.kayak.com › flight-routes › Chicago-Midway-MDW

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   The cheapest return flight ticket from Chicago Midway Airport to Boston found by KAYAK users in the last 72 hours was for $100 on Frontier, followed by Southwest ($270). One-way flight deals have also been found from as low as $50 on Frontier and from $107 on Allegiant Air.