Many airlines offer flexible change policies
Sign up to receive text alerts about your trip
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
Prices starting at $79 for return flights and $40 for one-way flights to Boston were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
|Origin Airport IATA Code||CHI|
|Destination Airport IATA Code||BOS|
|Direct Flight Airlines||American Airlines, KLM, Qatar Airways, JAL, Emirates, Delta Air Lines, Air New Zealand, United Airlines, Alaska Airlines, JetBlue Airways, Royal Jordanian, SAS, Hawaiian Airlines, Iberia, ANA, Virgin Atlantic, British Airways|
|Earliest Flight Arrival||2:18PM UTC|
|Latest Flight Arrival||3:20AM UTC|
TSA ARE VERY RUDE. for a person that has flown twice since 9/11, 1st time tsa took my lucky coins, this time they were just plain rude! I can't read minds and you are scared to move wrong and if you don't. Over fast enough, they are just plain hateful.
Our attendants on this flight were so kind and helpful! They were very friendly and personable!
Great flight with Delta
Hated the extra cost of buying seats to guarantee that we sat together. Not sure I would do this again. The value isn’t there.
I liked that I was allowed early boarding with my 4 year old. Not every airline allows that. Delta is great!
Wifi would not work and USB port was broke
Seats are so tight and small. But you get what you pay for.
First time on Jet Blue and it was a good experience
Great airline. I wish they had more routes.
Orbitz is the best online spot to find cheap tickets to put the wind beneath your wings for flights from Chicago to Boston you'll have a few extra bucks in your back pocket when you land in Beantown.
The Windy City offers two options for budget fares for your Chicago to Boston flight, depending on your location and personal tastes. O'Hare International Airport (ORD) is in the northwest corner, 17 miles from the downtown loop. Midway International Airport (MDW) is on the southwest side, eight miles from the loop. Budget-conscious planners who opt for O'Hare will find that the bustling airport, the world's second largest, is a hub for United Airlines and American Airlines and that the smaller Midway is a hub for Southwest Airlines. Your Chicago to Boston flight could be on any of the major airlines, because they all serve Massachusetts' capital city with direct flights. O'Hare offers the best in airport accommodations with a handful of lounges, classic American and international food, and a lot of specialty shops to procure a one-of-a-kind souvenir.
Even though the two-hour nonstop Chicago to Boston flight is a domestic route, you will step into a historic city known as the Athens of America when you land at Logan International Airport (BOS). Aviation.com dubbed Logan the "Easiest Airport to Get To" in 2007 because of its transportation options, including rental cars, cabs, vans, limos and several options from the Massachusetts Bay Transportation Authority (MBTA) like the Blue line train, the Silver line train, and the ferry. That means it is easy to enjoy your flight from Chicago to Boston without having to think about any other hassles, whether you're traveling the three miles to downtown or you're a budget planner who plotted tours of the City on a Hill when you booked tickets. If you're coming from Chicago, the weather in Boston will be nothing new, but chances are you'll want to book your flight from Chicago to Boston in the summer.
Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.