Selected fares from Chicago to Boston
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
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.
Save more with Boston Flight + Hotel packages
Bedford Plaza Hotel - Boston
2.5 out of 5.0Thu, Sep 21 - Mon, Sep 25
CHI-All Airports - Logan Intl.
$300
per person
W Boston
4.0 out of 5.0Thu, Sep 21 - Mon, Sep 25
CHI-All Airports - Logan Intl.
$612
per person
Kimpton Marlowe Hotel
4.0 out of 5.0Thu, Sep 21 - Mon, Sep 25
CHI-All Airports - Logan Intl.
$571
per person
The Midtown Hotel
2.5 out of 5.0Thu, Oct 5 - Mon, Oct 9
CHI-All Airports - Logan Intl.
$635
per person
Quality Inn & Suites Lexington
2.5 out of 5.0Thu, Sep 21 - Mon, Sep 25
CHI-All Airports - Logan Intl.
$330
per person
Hyatt Regency Boston Harbor
4.0 out of 5.0Thu, Sep 21 - Mon, Sep 25
CHI-All Airports - Logan Intl.
$623
per person
Royal Sonesta Boston
4.0 out of 5.0Thu, Oct 5 - Mon, Oct 9
CHI-All Airports - Logan Intl.
$878
per person
Ashworth by the Sea
3.0 out of 5.0Sat, Oct 14 - Wed, Oct 18
O'Hare Intl. - Logan Intl.
$280
per person
Red Roof PLUS+ Boston - Woburn
2.5 out of 5.0Thu, Sep 21 - Mon, Sep 25
CHI-All Airports - Logan Intl.
$365
per person
Hotel Veritas
3.5 out of 5.0Thu, Sep 21 - Mon, Sep 25
CHI-All Airports - Logan Intl.
$861
per person
Ramada Inn Boston
2.5 out of 5.0Thu, Sep 21 - Mon, Sep 25
CHI-All Airports - Logan Intl.
$451
per person
Courtyard by Marriott Woburn/Boston North
3.0 out of 5.0Thu, Oct 5 - Mon, Oct 9
CHI-All Airports - Logan Intl.
$580
per person
More to explore for Chicago to Boston
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Flights from Cities near Chicago
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Other Flights to Boston
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Other Flights from Chicago
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- Chicago to Denver
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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.
