Airfarewatchdog

Cheap Flights From Chicago, Illinois To Boston, Massachusetts

Chicago
Fare Alerts
  • Real deals from your departure city
  • Verified by our Dealhounds

Airfare Details for flights from Chicago to Boston

Search Now for Low Fares
 
Find Flights
Sorry this deal is over or has been sold out! But here’s another great Airfarewatchdog verified fare for this route!

$128 RT flight from Chicago to Boston (ORD-BOS)

  • Airline(s):
    Spirit Airlines
  • Seats are:
    Scarce
  • More Details:
    Fall Travel, Select Travel Dates Only!
  • Last Updated:
    Tuesday, June 18, 2013
  • Our Notes:
    Select dates October through December. Some routes will end in November. For specific dates available, view the sale page at Spirit.com. Lower fares may ...morebe available for Spirit's $9 fare club members. This fare only includes one small "personal item" carry-on that does not exceed 16x14x12 inches. Larger carry-on or checked baggage require an additional charge. To get this fare, you must also accept a Spirit assigned seat at check-in and print your boarding pass at home or at an airport kiosk. Choosing a specific seat or using a human airport agent requires additional charges. This fare includes Spirit.com's $17.98 passenger usage fee, which can be avoided by booking at an airport counter. This sale ends at 11:59pm ET on Jun. 19, 2013.
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.

Are Your Travel Dates Set? Check Fares Now:

 




Find Flights
Check out these top-rated hotels in Boston
As rated by TripAdvisor® travelers
Show the lowest price for this hotel*
*from our partners
"It's the Little Things....." 06/18/2013
"Overnight for a Red Sox Game" 06/18/2013
Show the lowest price for this hotel*
*from our partners
"Good hotel, Disappointing Service at Rooftop Bar" 06/17/2013
"Luxury Hotel right off Boston Commons" 06/16/2013
Show the lowest price for this hotel*
*from our partners
"Stay of a Lifetime" 06/16/2013
"Perfect by the park" 06/10/2013

More Flights From Chicago To Boston (ORD-BOS)

Price
Details
$218 RT Non-Stop Flights. No min. stay. Travel between Aug. 26 - Dec. 18, 2013 (American, JetBlue, United) See all details »
  • Airline(s):
    American, JetBlue, United
  • Seats are:
    Limited Availability
  • Available for travel:
    Exc Fri/Sun
  • Travel by:
    Wednesday, December 18, 2013
  • More Details:
    Non-Stop Flights, No Min. Stay, Travel Between Aug. 26 - Dec. 18, 2013
  • Last Updated:
    Wednesday, June 19, 2013
  • Our Notes:
    We Found Travel Departing Sep 19 And Returning Sep 26.

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
$308 Flight from O'Hare to Boston (ORD-BOS) Wed, Jun 19 - Tue, Jul 2 Spirit Airlines
$313 Flight from O'Hare to Boston (ORD-BOS) Wed, Jun 19 - Mon, Jun 24 Spirit Airlines
$318 Flight from O'Hare to Boston (ORD-BOS) Wed, Jun 19 - Sat, Jun 22 Spirit Airlines
$331 Flight from O'Hare to Boston (ORD-BOS) Wed, Jun 19 - Thu, Jun 20 United Airlines
$342 Flight from O'Hare to Boston (ORD-BOS) Wed, Jun 19 - Fri, Jun 21 Delta Air Lines
$342 Flight from O'Hare to Boston (ORD-BOS) Thu, Jun 20 - Fri, Jun 21 Delta Air Lines
$391 Flight from O'Hare to Boston (ORD-BOS) Thu, Jun 20 - Thu, Jun 20 American Airlines
$400 Flight from O'Hare to Boston (ORD-BOS) Wed, Jun 19 - Fri, Jun 21 American Airlines
$411 Flight from O'Hare to Boston (ORD-BOS) Wed, Jun 19 - Fri, Jun 21 American Airlines
$451 Flight from O'Hare to Boston (ORD-BOS) Wed, Jun 19 - Thu, Jun 20 American Airlines
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).
Advertisement
Advertisement
Advertisement
Advertisement
http://rd.airfarewatchdog.com/?ad_user_tracking=%5Bsource%3D%2Ctaparam%3D%2Csupmt%3D%5D