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Cheap Flights From Chicago, Illinois (ORD) To Boston, Massachusetts (BOS)

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Fares from Chicago, IL (ORD)
$161 RT to
Boston, MA (BOS)
Sorry this deal is over or has been sold out! But here’s another great Airfarewatchdog verified fare for this route!
$161 RT Chicago to Boston, MA
Airline(s)
United, American, JetBlue
Seats:
Seats are not available on all flights or all dates of travel. You may need to have flexible travel dates to find this fare. Fares for travel on holidays may be higher.
Adv. Purchase:
21 Days
Travel Ending:
Saturday, 04 April 2015
More Details:
Non-Stop Flights, No min. stay, No peak holiday travel at this price
Last Updated:
Monday, 20 October 2014
Our Notes:
Slightly higher price for travel through June 17 on JetBlue. We found seats for departure Jan. 13 and return Jan. 20. There are other dates available as well. CheapAir.com will include a booking fee of $9.95.
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All mandatory taxes/fees are included in the price. Tax-inclusive fare may be a few dollars higher or lower depending on the airport you connect through, if any. Baggage fees, if applicable, and other optional fees are not included.

Our Dealhounds found this airfare using flexible date search. This means we searched a range of dates to find you the best price.

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More Flights From Chicago To Boston (ORD-BOS)

Price
Details
$161 RT Lowest fare found for travel within the next 30 days. (United, American) See all details »
  • Airline(s):
    United, American
  • Seats are:
    Seats Are Not Available On All Flights Or All Dates Of Travel. You May Need To Have Flexible Travel Dates To Find This Fare. Fares For Travel On Holidays May Be Higher.
  • Advance Purchase:
    22 Days
  • Available for travel:
    Tue-Wed
  • Travel starting:
    Tuesday, 11 November 2014
  • More Details:
    Lowest Fare Found For Travel Within The Next 30 Days.
  • Last Updated:
    Monday, October 20, 2014

Reviews for Chicago to Boston (ORD-BOS)

based on 8 reviews
Flown this route before? Write a review
    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Tight Squeeze

    by Jandy on June 10, 2011

    Flight from Chicago to Boston

    Airline:
    American
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    May 2011
    Seat Class:
    economy

    Seats were close together; felt very cramped. Overall the flight was good and the price I paid to travel was GREAT.

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Outbound Great

    by Teampedersen on February 24, 2011

    Flight from Chicago to Boston

    Airline:
    American
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    February 2011
    Seat Class:
    economy

    I got a great deal on this flight - $159 round trip. The outbound was almost empty. Flying on a Sunday morning must have helped. Inbound was delayed 1/2 hour and very crowded but uneventful. On the last few flights I've taken on American they have valeted my bag at the gate. I'm always happy to avoid both the $25 bag fee and the hassle of carrying on my weekend bag.

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Smooth and on time

    by sshoemaker on October 1, 2010

    Flight from Chicago to Boston

    Airline:
    American
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    September 2010
    Seat Class:
    economy

    The flight left on time and arrived on time! It was a pleasant trip and good service. A positive experience.

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    American Airlines

    by ujo24 on September 9, 2010

    Flight from Chicago to Boston

    Airline:
    American
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    September 2010
    Seat Class:
    economy

    I recently flew American and the flight was on time and the staff was just fine, but the seats were awefully small. I'm a 6'0" male and luckily there were 2 women in my row with me. Felt like I was at a ball game. American has a good name, at least I thought, don't make it a cattle car like some other airlines.

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Comfortable, easy flight.

    by runof10 on July 28, 2010

    Flight from Chicago to Boston

    Airline:
    United
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    July 2010
    Seat Class:
    economy

    A comfortable, easy, 2+ hour non-stop flight. United is a great airline, but be aware of the baggage fee's. Save money, and purchase online before you go to the airport.

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    No frills...Like getting on a bus.

    by audears on July 22, 2010

    Flight from Chicago to Boston

    Airline:
    American
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    July 2010
    Seat Class:
    economy

    Check in and security lines were ridiculously long (even at 5:00AM on a Friday morning!) Definitely not enough ground personnel on either leg of the trip. Plane ride fairly uneventful. Loved the pilot--we came in early, yet had to sit on the ground for 1/2 an hour waiting for a gate/ground crew. He made the announcement that he wasn't going to make excuses for his company (AA), and that he had contacted them giving our ETA, but the ground crew went to lunch anyway, so we had to wait. His honesty was refreshing and appreciated!

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Typical

    by EFH on June 2, 2010

    Flight from Chicago to Boston

    Airline:
    American
    RT/OW
    Round Trip
    Number of Stops:
    No stops
    Date of Flight:
    May 2010
    Seat Class:
    economy

    Following nearly an hour wait for wheelchair at ORD, during which several with higher numbers were helped and we were ignored, we finally had to race to the gate with a quick stop for carry-on breakfast for a flight that was 15 minutes delayed (why?). Once on flight, while it was completely full, we were treated well.

    Note that on the return - also full - flight, only problem was passenger bringing their dog on with them. Don't these folks care that some of us are ALLERGIC to their dogs?? Otherwise, well treated by American, as usual.

    1. Flight Rating

    2. Check-in Experience:

    3. In-flight Service:

    4. Seat Comfort:

    Pleasant but with delay

    by donnybrook on May 6, 2010

    Flight from Chicago to Boston

    Airline:
    American
    Number of Stops:
    No stops
    Date of Flight:
    April 2010
    Seat Class:
    economy

    Was set to fly out of O'Hare to Boston on 4/30 at 9:40pm. Arrived at the gate around 8:15pm and found out the flight had been delayed and was now set to take off at 10:45.

    We didn't leave until 11:00pm, giving us touchdown in Boston at 2:00am local time.

    Slept the entire flight so I take it was a smooth ride, overall.

    A 1:20 delay isn't that bad in the grand scheme of things but I do feel like I've had more delays than usual on AA.

Flown this route before? Write a review
Sample Fares found by other travelers within the past 72 hours
Price From/To Depart/Return Airline
$282 Flight from O'Hare to Boston (ORD-BOS) Thu, Jun 5 - Wed, Jun 11 Delta Air Lines
$282 Flight from O'Hare to Boston (ORD-BOS) Thu, Jun 5 - Tue, Jun 10 Delta Air Lines
$292 Flight from O'Hare to Boston (ORD-BOS) Thu, Jun 5 - Sun, Jun 8 Delta Air Lines
$292 Flight from O'Hare to Boston (ORD-BOS) Thu, Jun 5 - Fri, Jun 6 Delta Air Lines
$355 Flight from O'Hare to Boston (ORD-BOS) Thu, Jun 5 - Sat, Jun 7 Delta Air Lines
$365 Flight from O'Hare to Boston (ORD-BOS) Thu, Jun 5 - Mon, Jun 9 Delta Air Lines
$379 Flight from O'Hare to Boston (ORD-BOS) Thu, Jun 5 - Tue, Jun 10 Delta Air Lines
$379 Flight from O'Hare to Boston (ORD-BOS) Thu, Jun 5 - Mon, Jun 9 Delta Air Lines
$379 Flight from O'Hare to Boston (ORD-BOS) Thu, Jun 5 - Sat, Jun 7 Delta Air Lines
$405 Flight from O'Hare to Boston (ORD-BOS) Thu, Jun 5 - Sun, Jun 8 Delta Air Lines
There are approximately 812 flights covering the route from O'Hare International Airport in Chicago to Logan International Airport in Boston, provided by as many as 9 airlines.

The following airlines sometimes offer nonstop cheap flights from Chicago to Boston:

Transwest Air

As an alternative to flying from Chicago, you may also want to try searching for cheap flights from Rockford (RFD).
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