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Flights from Chicago to Boston (CHI to BOS)

Discover alternate routes & cheap one way flights from Chicago to Boston (CHI to BOS) within a departure date range.

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  • USD 51
    Frontier AirlinesSpirit Airlines
    4:15pm - 7:16am
    Wed Feb 8th
    14h 1m
    Chicago (ORD) → Boston (BOS)
    1 Stop

    Wed Feb 8th 2023 Frontier Airlines · F9 1575 Depart at 4:15 pm from Chicago (ORD) Fly for 2h 5m Arrive at 7:20 pm in Atlanta (ATL)

    Layover in Atlanta for 9h 35m

    Thu Feb 9th 2023 Spirit Airlines · NK 1444 Depart at 4:55 am from Atlanta (ATL) Fly for 2h 21m Arrive at 7:16 am in Boston (BOS)

  • USD 52
    United Airlines
    2:31am - 5:45am
    Tue Jan 24th
    2h 14m
    Chicago (ORD) → Boston (BOS)
    Direct

    Tue Jan 24th 2023 United Airlines · UA 1803 Depart at 2:31 am from Chicago (ORD) Fly for 2h 14m Arrive at 5:45 am in Boston (BOS)

  • USD 51
    Frontier AirlinesSpirit Airlines
    4:15pm - 8:20am
    Tue Feb 7th
    15h 5m
    Chicago (ORD) → Boston (BOS)
    1 Stop

    Tue Feb 7th 2023 Frontier Airlines · F9 1575 Depart at 4:15 pm from Chicago (ORD) Fly for 2h 5m Arrive at 7:20 pm in Atlanta (ATL)

    Layover in Atlanta for 10h 37m

    Wed Feb 8th 2023 Spirit Airlines · NK 1444 Depart at 5:57 am from Atlanta (ATL) Fly for 2h 23m Arrive at 8:20 am in Boston (BOS)

  • USD 52
    United Airlines
    2:31am - 5:45am
    Wed Feb 8th
    2h 14m
    Chicago (ORD) → Boston (BOS)
    Direct

    Wed Feb 8th 2023 United Airlines · UA 1803 Depart at 2:31 am from Chicago (ORD) Fly for 2h 14m Arrive at 5:45 am in Boston (BOS)

  • USD 67
    American Airlines
    4:00pm - 7:07pm
    Wed Jan 18th
    2h 7m
    Chicago (ORD) → Boston (BOS)
    Direct

    Wed Jan 18th 2023 American Airlines · AA 2682 Depart at 4:00 pm from Chicago (ORD) Fly for 2h 7m Arrive at 7:07 pm in Boston (BOS)

  • USD 51
    Frontier AirlinesSpirit Airlines
    4:15pm - 8:25am
    Tue Jan 31st
    15h 10m
    Chicago (ORD) → Boston (BOS)
    1 Stop

    Tue Jan 31st 2023 Frontier Airlines · F9 1575 Depart at 4:15 pm from Chicago (ORD) Fly for 2h 5m Arrive at 7:20 pm in Atlanta (ATL)

    Layover in Atlanta for 10h 37m

    Wed Feb 1st 2023 Spirit Airlines · NK 1444 Depart at 5:57 am from Atlanta (ATL) Fly for 2h 28m Arrive at 8:25 am in Boston (BOS)

  • USD 52
    United Airlines
    2:31am - 5:45am
    Tue Jan 31st
    2h 14m
    Chicago (ORD) → Boston (BOS)
    Direct

    Tue Jan 31st 2023 United Airlines · UA 1803 Depart at 2:31 am from Chicago (ORD) Fly for 2h 14m Arrive at 5:45 am in Boston (BOS)

  • USD 67
    American Airlines
    4:00pm - 7:07pm
    Wed Feb 1st
    2h 7m
    Chicago (ORD) → Boston (BOS)
    Direct

    Wed Feb 1st 2023 American Airlines · AA 2682 Depart at 4:00 pm from Chicago (ORD) Fly for 2h 7m Arrive at 7:07 pm in Boston (BOS)

  • USD 51
    Frontier AirlinesSpirit Airlines
    4:15pm - 8:25am
    Wed Feb 1st
    15h 10m
    Chicago (ORD) → Boston (BOS)
    1 Stop

    Wed Feb 1st 2023 Frontier Airlines · F9 1575 Depart at 4:15 pm from Chicago (ORD) Fly for 2h 5m Arrive at 7:20 pm in Atlanta (ATL)

    Layover in Atlanta for 10h 37m

    Thu Feb 2nd 2023 Spirit Airlines · NK 1444 Depart at 5:57 am from Atlanta (ATL) Fly for 2h 28m Arrive at 8:25 am in Boston (BOS)

  • USD 52
    United Airlines
    2:31am - 5:45am
    Wed Feb 1st
    2h 14m
    Chicago (ORD) → Boston (BOS)
    Direct

    Wed Feb 1st 2023 United Airlines · UA 1803 Depart at 2:31 am from Chicago (ORD) Fly for 2h 14m Arrive at 5:45 am in Boston (BOS)

  • USD 67
    American Airlines
    4:00pm - 7:07pm
    Mon Jan 30th
    2h 7m
    Chicago (ORD) → Boston (BOS)
    Direct

    Mon Jan 30th 2023 American Airlines · AA 2682 Depart at 4:00 pm from Chicago (ORD) Fly for 2h 7m Arrive at 7:07 pm in Boston (BOS)

  • USD 51
    Frontier AirlinesSpirit Airlines
    4:15pm - 8:25am
    Sat Feb 4th
    15h 10m
    Chicago (ORD) → Boston (BOS)
    1 Stop

    Sat Feb 4th 2023 Frontier Airlines · F9 1575 Depart at 4:15 pm from Chicago (ORD) Fly for 2h 5m Arrive at 7:20 pm in Atlanta (ATL)

    Layover in Atlanta for 10h 37m

    Sun Feb 5th 2023 Spirit Airlines · NK 1444 Depart at 5:57 am from Atlanta (ATL) Fly for 2h 28m Arrive at 8:25 am in Boston (BOS)

  • USD 52
    United Airlines
    2:31am - 5:45am
    Tue Feb 7th
    2h 14m
    Chicago (ORD) → Boston (BOS)
    Direct

    Tue Feb 7th 2023 United Airlines · UA 1803 Depart at 2:31 am from Chicago (ORD) Fly for 2h 14m Arrive at 5:45 am in Boston (BOS)

  • USD 67
    American Airlines
    4:00pm - 7:07pm
    Tue Jan 24th
    2h 7m
    Chicago (ORD) → Boston (BOS)
    Direct

    Tue Jan 24th 2023 American Airlines · AA 2682 Depart at 4:00 pm from Chicago (ORD) Fly for 2h 7m Arrive at 7:07 pm in Boston (BOS)

  • USD 51
    Frontier AirlinesSpirit Airlines
    4:15pm - 8:25am
    Tue Jan 24th
    15h 10m
    Chicago (ORD) → Boston (BOS)
    1 Stop

    Tue Jan 24th 2023 Frontier Airlines · F9 1575 Depart at 4:15 pm from Chicago (ORD) Fly for 2h 5m Arrive at 7:20 pm in Atlanta (ATL)

    Layover in Atlanta for 10h 37m

    Wed Jan 25th 2023 Spirit Airlines · NK 1444 Depart at 5:57 am from Atlanta (ATL) Fly for 2h 28m Arrive at 8:25 am in Boston (BOS)

  • USD 52
    United Airlines
    2:31am - 5:45am
    Wed Jan 25th
    2h 14m
    Chicago (ORD) → Boston (BOS)
    Direct

    Wed Jan 25th 2023 United Airlines · UA 1803 Depart at 2:31 am from Chicago (ORD) Fly for 2h 14m Arrive at 5:45 am in Boston (BOS)

  • USD 67
    American Airlines
    4:00pm - 7:07pm
    Tue Jan 31st
    2h 7m
    Chicago (ORD) → Boston (BOS)
    Direct

    Tue Jan 31st 2023 American Airlines · AA 2682 Depart at 4:00 pm from Chicago (ORD) Fly for 2h 7m Arrive at 7:07 pm in Boston (BOS)

  • USD 52
    United Airlines
    8:00am - 11:21am
    Wed Jan 25th
    2h 21m
    Chicago (ORD) → Boston (BOS)
    Direct

    Wed Jan 25th 2023 United Airlines · UA 1847 Depart at 8:00 am from Chicago (ORD) Fly for 2h 21m Arrive at 11:21 am in Boston (BOS)

  • USD 52
    United Airlines
    5:59am - 9:20am
    Wed Feb 8th
    2h 21m
    Chicago (ORD) → Boston (BOS)
    Direct

    Wed Feb 8th 2023 United Airlines · UA 2091 Depart at 5:59 am from Chicago (ORD) Fly for 2h 21m Arrive at 9:20 am in Boston (BOS)

  • USD 53
    JetBlue Airways
    6:04am - 9:23am
    Tue Jan 17th
    2h 19m
    Chicago (ORD) → Boston (BOS)
    Direct

    Tue Jan 17th 2023 JetBlue Airways · B6 312 Depart at 6:04 am from Chicago (ORD) Fly for 2h 19m Arrive at 9:23 am in Boston (BOS)

  • USD 53
    JetBlue Airways
    6:04am - 9:23am
    Wed Jan 18th
    2h 19m
    Chicago (ORD) → Boston (BOS)
    Direct

    Wed Jan 18th 2023 JetBlue Airways · B6 312 Depart at 6:04 am from Chicago (ORD) Fly for 2h 19m Arrive at 9:23 am in Boston (BOS)

  • USD 62
    United Airlines
    2:31am - 5:45am
    Sat Jan 21st
    2h 14m
    Chicago (ORD) → Boston (BOS)
    Direct

    Sat Jan 21st 2023 United Airlines · UA 1803 Depart at 2:31 am from Chicago (ORD) Fly for 2h 14m Arrive at 5:45 am in Boston (BOS)

  • USD 62
    United Airlines
    9:08am - 12:28pm
    Fri Jan 20th
    2h 20m
    Chicago (ORD) → Boston (BOS)
    Direct

    Fri Jan 20th 2023 United Airlines · UA 2306 Depart at 9:08 am from Chicago (ORD) Fly for 2h 20m Arrive at 12:28 pm in Boston (BOS)

  • USD 62
    United Airlines
    9:08am - 12:28pm
    Thu Jan 19th
    2h 20m
    Chicago (ORD) → Boston (BOS)
    Direct

    Thu Jan 19th 2023 United Airlines · UA 2306 Depart at 9:08 am from Chicago (ORD) Fly for 2h 20m Arrive at 12:28 pm in Boston (BOS)

  • USD 62
    United Airlines
    1:00pm - 4:20pm
    Fri Jan 20th
    2h 20m
    Chicago (ORD) → Boston (BOS)
    Direct

    Fri Jan 20th 2023 United Airlines · UA 2157 Depart at 1:00 pm from Chicago (ORD) Fly for 2h 20m Arrive at 4:20 pm in Boston (BOS)

  • USD 51
    Frontier AirlinesSpirit Airlines
    4:15pm - 8:25am
    Wed Jan 25th
    15h 10m
    Chicago (ORD) → Boston (BOS)
    1 Stop

    Wed Jan 25th 2023 Frontier Airlines · F9 1575 Depart at 4:15 pm from Chicago (ORD) Fly for 2h 5m Arrive at 7:20 pm in Atlanta (ATL)

    Layover in Atlanta for 10h 37m

    Thu Jan 26th 2023 Spirit Airlines · NK 1444 Depart at 5:57 am from Atlanta (ATL) Fly for 2h 28m Arrive at 8:25 am in Boston (BOS)

  • USD 52
    United Airlines
    1:00pm - 4:20pm
    Wed Feb 1st
    2h 20m
    Chicago (ORD) → Boston (BOS)
    Direct

    Wed Feb 1st 2023 United Airlines · UA 2157 Depart at 1:00 pm from Chicago (ORD) Fly for 2h 20m Arrive at 4:20 pm in Boston (BOS)

  • USD 67
    American Airlines
    4:00pm - 7:07pm
    Thu Jan 26th
    2h 7m
    Chicago (ORD) → Boston (BOS)
    Direct

    Thu Jan 26th 2023 American Airlines · AA 2682 Depart at 4:00 pm from Chicago (ORD) Fly for 2h 7m Arrive at 7:07 pm in Boston (BOS)

  • USD 51
    Frontier AirlinesSpirit Airlines
    9:44am - 7:16am
    Wed Feb 8th
    20h 32m
    Chicago (MDW) → Boston (BOS)
    1 Stop

    Wed Feb 8th 2023 Frontier Airlines · F9 1355 Depart at 9:44 am from Chicago (MDW) Fly for 1h 58m Arrive at 12:42 pm in Atlanta (ATL)

    Layover in Atlanta for 16h 13m

    Thu Feb 9th 2023 Spirit Airlines · NK 1444 Depart at 4:55 am from Atlanta (ATL) Fly for 2h 21m Arrive at 7:16 am in Boston (BOS)

  • USD 52
    United Airlines
    1:00pm - 4:20pm
    Tue Jan 24th
    2h 20m
    Chicago (ORD) → Boston (BOS)
    Direct

    Tue Jan 24th 2023 United Airlines · UA 2157 Depart at 1:00 pm from Chicago (ORD) Fly for 2h 20m Arrive at 4:20 pm in Boston (BOS)

  • USD 67
    American Airlines
    4:00pm - 7:07pm
    Sun Jan 29th
    2h 7m
    Chicago (ORD) → Boston (BOS)
    Direct

    Sun Jan 29th 2023 American Airlines · AA 2682 Depart at 4:00 pm from Chicago (ORD) Fly for 2h 7m Arrive at 7:07 pm in Boston (BOS)

  • USD 51
    Frontier AirlinesSpirit Airlines
    9:44am - 8:20am
    Tue Feb 7th
    21h 36m
    Chicago (MDW) → Boston (BOS)
    1 Stop

    Tue Feb 7th 2023 Frontier Airlines · F9 1355 Depart at 9:44 am from Chicago (MDW) Fly for 1h 58m Arrive at 12:42 pm in Atlanta (ATL)

    Layover in Atlanta for 17h 15m

    Wed Feb 8th 2023 Spirit Airlines · NK 1444 Depart at 5:57 am from Atlanta (ATL) Fly for 2h 23m Arrive at 8:20 am in Boston (BOS)

  • USD 52
    United Airlines
    1:00pm - 4:20pm
    Tue Jan 31st
    2h 20m
    Chicago (ORD) → Boston (BOS)
    Direct

    Tue Jan 31st 2023 United Airlines · UA 2157 Depart at 1:00 pm from Chicago (ORD) Fly for 2h 20m Arrive at 4:20 pm in Boston (BOS)

  • USD 67
    American Airlines
    4:00pm - 7:07pm
    Thu Feb 2nd
    2h 7m
    Chicago (ORD) → Boston (BOS)
    Direct

    Thu Feb 2nd 2023 American Airlines · AA 2682 Depart at 4:00 pm from Chicago (ORD) Fly for 2h 7m Arrive at 7:07 pm in Boston (BOS)

  • USD 51
    Frontier AirlinesSpirit Airlines
    9:44am - 8:25am
    Thu Jan 26th
    21h 41m
    Chicago (MDW) → Boston (BOS)
    1 Stop

    Thu Jan 26th 2023 Frontier Airlines · F9 1355 Depart at 9:44 am from Chicago (MDW) Fly for 1h 58m Arrive at 12:42 pm in Atlanta (ATL)

    Layover in Atlanta for 17h 15m

    Fri Jan 27th 2023 Spirit Airlines · NK 1444 Depart at 5:57 am from Atlanta (ATL) Fly for 2h 28m Arrive at 8:25 am in Boston (BOS)

  • USD 52
    United Airlines
    5:59am - 9:20am
    Tue Feb 7th
    2h 21m
    Chicago (ORD) → Boston (BOS)
    Direct

    Tue Feb 7th 2023 United Airlines · UA 2091 Depart at 5:59 am from Chicago (ORD) Fly for 2h 21m Arrive at 9:20 am in Boston (BOS)

  • USD 67
    American Airlines
    4:00pm - 7:07pm
    Wed Jan 25th
    2h 7m
    Chicago (ORD) → Boston (BOS)
    Direct

    Wed Jan 25th 2023 American Airlines · AA 2682 Depart at 4:00 pm from Chicago (ORD) Fly for 2h 7m Arrive at 7:07 pm in Boston (BOS)

  • USD 52
    United Airlines
    5:59am - 9:20am
    Wed Jan 18th
    2h 21m
    Chicago (ORD) → Boston (BOS)
    Direct

    Wed Jan 18th 2023 United Airlines · UA 2091 Depart at 5:59 am from Chicago (ORD) Fly for 2h 21m Arrive at 9:20 am in Boston (BOS)

  • USD 67
    American Airlines
    4:00pm - 7:07pm
    Fri Jan 27th
    2h 7m
    Chicago (ORD) → Boston (BOS)
    Direct

    Fri Jan 27th 2023 American Airlines · AA 2682 Depart at 4:00 pm from Chicago (ORD) Fly for 2h 7m Arrive at 7:07 pm in Boston (BOS)

  • USD 52
    United Airlines
    8:00am - 11:21am
    Wed Feb 8th
    2h 21m
    Chicago (ORD) → Boston (BOS)
    Direct

    Wed Feb 8th 2023 United Airlines · UA 1847 Depart at 8:00 am from Chicago (ORD) Fly for 2h 21m Arrive at 11:21 am in Boston (BOS)

  • USD 52
    United Airlines
    5:59am - 9:20am
    Tue Jan 31st
    2h 21m
    Chicago (ORD) → Boston (BOS)
    Direct

    Tue Jan 31st 2023 United Airlines · UA 2091 Depart at 5:59 am from Chicago (ORD) Fly for 2h 21m Arrive at 9:20 am in Boston (BOS)

  • USD 52
    United Airlines
    5:59am - 9:20am
    Tue Jan 24th
    2h 21m
    Chicago (ORD) → Boston (BOS)
    Direct

    Tue Jan 24th 2023 United Airlines · UA 2091 Depart at 5:59 am from Chicago (ORD) Fly for 2h 21m Arrive at 9:20 am in Boston (BOS)

  • USD 52
    United Airlines
    5:59am - 9:20am
    Wed Jan 25th
    2h 21m
    Chicago (ORD) → Boston (BOS)
    Direct

    Wed Jan 25th 2023 United Airlines · UA 2091 Depart at 5:59 am from Chicago (ORD) Fly for 2h 21m Arrive at 9:20 am in Boston (BOS)

  • USD 52
    United Airlines
    8:00am - 11:21am
    Tue Feb 7th
    2h 21m
    Chicago (ORD) → Boston (BOS)
    Direct

    Tue Feb 7th 2023 United Airlines · UA 1847 Depart at 8:00 am from Chicago (ORD) Fly for 2h 21m Arrive at 11:21 am in Boston (BOS)

  • USD 52
    United Airlines
    8:00am - 11:21am
    Wed Feb 1st
    2h 21m
    Chicago (ORD) → Boston (BOS)
    Direct

    Wed Feb 1st 2023 United Airlines · UA 1847 Depart at 8:00 am from Chicago (ORD) Fly for 2h 21m Arrive at 11:21 am in Boston (BOS)

  • USD 52
    United Airlines
    5:59am - 9:20am
    Wed Feb 1st
    2h 21m
    Chicago (ORD) → Boston (BOS)
    Direct

    Wed Feb 1st 2023 United Airlines · UA 2091 Depart at 5:59 am from Chicago (ORD) Fly for 2h 21m Arrive at 9:20 am in Boston (BOS)

  • USD 52
    United Airlines
    8:00am - 11:21am
    Wed Jan 18th
    2h 21m
    Chicago (ORD) → Boston (BOS)
    Direct

    Wed Jan 18th 2023 United Airlines · UA 1847 Depart at 8:00 am from Chicago (ORD) Fly for 2h 21m Arrive at 11:21 am in Boston (BOS)

  • USD 52
    United Airlines
    8:00am - 11:21am
    Tue Jan 24th
    2h 21m
    Chicago (ORD) → Boston (BOS)
    Direct

    Tue Jan 24th 2023 United Airlines · UA 1847 Depart at 8:00 am from Chicago (ORD) Fly for 2h 21m Arrive at 11:21 am in Boston (BOS)

  • USD 62
    United Airlines
    8:00am - 11:21am
    Thu Jan 19th
    2h 21m
    Chicago (ORD) → Boston (BOS)
    Direct

    Thu Jan 19th 2023 United Airlines · UA 1847 Depart at 8:00 am from Chicago (ORD) Fly for 2h 21m Arrive at 11:21 am in Boston (BOS)

  • USD 62
    United Airlines
    8:00am - 11:21am
    Fri Jan 20th
    2h 21m
    Chicago (ORD) → Boston (BOS)
    Direct

    Fri Jan 20th 2023 United Airlines · UA 1847 Depart at 8:00 am from Chicago (ORD) Fly for 2h 21m Arrive at 11:21 am in Boston (BOS)

@sarahbb1
Sarah Belizaire
@sarahbb1

Have flexible travel plans or looking for alternative routes given the chaos? Check out all the connection possibilities via a super helpful site created by @ismaelyws flightlist.io thanks to @andy_travels for the recommendation #travel #flights

@eyupitsjohn
John Ford
@eyupitsjohn

There seem to be lots of sites launching at the moment that promise to find you cheap one way flights but not many have the professional finish of Flightlist by @ismaelyws #travel #flights

@andy_travels
Andy Travels
@andy_travels

@ismaelyws Just tried out Flightlist for the first time. Really nice idea, well made, and just what I need at the moment 👍

@travelwitbender
Travel With Bender
@travelwitbender

Did you spot my recent article about how to score cheap one way flights? ✈️ FlightList is my new secret tool for discovering cheap routes, within a departure date range. Plus you can also search by country/region for departures & destinations. Powerful! 💪

Explore Flight Options

Cheap Flight Search Tips

Tips to help you find the cheapest flights from Chicago to Boston (CHI to BOS).

  • Book 45-90 days before your departure date.
  • Fly during weekdays (Monday-Thursday).
  • Airfare Sales: Airlines sometimes offer huge discounts and since we take a bottom-up approach these flights will appear first in the results, so check back regularly because they don't usually last long.

Why I Built FlightList

❝As someone who works remotely & travels frequently, I always book one way flights and I'm flexible on my departure dates. I look for the best deals. Most sites require you to enter a specific departure date and clutter the page with uneccessary options, images and ads. I want something simple and minimal which allows me to search by departure date range & display a list of flights with the ability to filter according to my needs. So, I built FlightList to solve my own problem & help other travelers who may have the same frustration. It's how I imagine a flight booking site should be.❞

- Hans Desjarlais, Founder & Creator Hans Desjarlais