Cheap Flight Deals From Chicago (CHI) to Boston (BOS) Starting at $69

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Airfares from $69 One Way, $138 Round Trip from Chicago to Boston

Prices starting at $138 for return flights and $69 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.

Boston economy flight packages

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Sheraton Boston Needham Hotel
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More About Flying To Boston from Chicago

Route Information for Flights from Chicago to Boston

Origin Airport IATA Code CHI
Destination Airport IATA Code BOS
Distance 863 mi
Direct Flight Airlines American Airlines, KLM, Qatar Airways, JAL, Azul, Emirates, Delta Air Lines, Air New Zealand, United Airlines, Alaska Airlines, JetBlue Airways, SAS, Royal Jordanian, Hawaiian Airlines, Korean Air, ANA, Virgin Atlantic, British Airways
Earliest Flight Arrival 1:30PM UTC
Latest Flight Arrival 5:00AM UTC

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). 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.

Frequently asked questions

Am I able to catch a flight from Chicago to Boston now?
Head to the Covid-19 Travel Advisor for the most up-to-date info on travel restrictions and quarantine requirements when flying from Chicago to Boston.
Are there non-stop flights from Chicago to Boston?
There are no less than 4 airlines that offer nonstop services from Chicago, IL (ORD-O’Hare Intl.) to Logan Intl. Airport. You won’t have to worry about sprinting to catch a connecting flight on this route! These are a few of the carriers you can book with:

  • United Airlines
  • American Airlines
  • Delta
  • JetBlue

What is the shortest flight from Chicago to Boston?
The trip from Chicago to Boston can be as fast as 2 hours and 59 minutes. With a leisurely flight time like this, why not take off on a spur-of-the-moment getaway?
What airlines fly from Chicago to Boston most frequently?
We all have our preferences when it comes to airlines, and you have a nice selection when flying from Chicago to Boston. These leading carriers fly this route most frequently: United Airlines - (UA) with 208 flights every month American Airlines - (AA) with 199 flights every month Delta - (DL) with 147 flights every month JetBlue - (B6) with 56 flights every month
If I am not able to travel due to COVID-19, can I cancel my flight to Boston?
We get that traveling right now has its challenges, so it’s good to know that many reservations booked through us are able to be cancelled or changed. If your travel plans to Boston have been affected by COVID-19, a lot of airlines are making things easier by offering credits to use at a later date. Just sign in to your account and you’ll quickly see what options are available. Our Customer Service Portal is the place to go for more information.
Are there flights to Boston with flexible change policies?
In most cases you’ll have the option to reschedule your flight to Boston without a change fee. All you have to do then is pay the difference between the old flight and the new one. Look for the “no change fees” filter and book with confidence.
What is the cheapest day of the week to fly?
Consider flying out early in the week to save on your airfare. Orbitz data from 2021 shows that Monday is the cheapest day to depart, followed by Tuesday. Saturday showed the highest average ticket prices likely because many travelers prefer to start their vacation on a weekend.
What is the cheapest month to fly?
We won’t keep you guessing, according to Orbitz data from 2021, the cheapest month to fly is February. Perfect for those who need a weekend getaway, or just a break from it all in the shortest month of the year. Be aware that the most expensive time to fly is during the height of summer in July, and in the holiday month of December.*According to flight demand on from January to December 2021. Savings are subject to change based on departure location, date and destination.

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.