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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
YOTEL Boston
3.5 out of 5.0Mon, Jul 23 - Sun, Jul 29
CHI-All Airports - Logan Intl.
$850 per person
Boston Marriott Burlington
3.5 out of 5.0Mon, Jul 23 - Sun, Jul 29
CHI-All Airports - Logan Intl.
$958 per person
Hilton Boston/Woburn
3.5 out of 5.0Mon, Jul 23 - Sun, Jul 29
CHI-All Airports - Logan Intl.
$531 per person
Holiday Inn Boston Bunker Hill Area
3.0 out of 5.0Mon, Jul 23 - Sun, Jul 29
CHI-All Airports - Logan Intl.
$784 per person
Crowne Plaza Boston - Newton
3.5 out of 5.0Mon, Jul 23 - Sun, Jul 29
CHI-All Airports - Logan Intl.
$707 per person
enVision Hotel Boston - Everett, an Ascend Collection Member
3.5 out of 5.0Mon, Jul 23 - Sun, Jul 29
CHI-All Airports - Logan Intl.
$786 per person
Sheraton Needham Hotel
3.5 out of 5.0Mon, Jul 23 - Sun, Jul 29
CHI-All Airports - Logan Intl.
$746 per person
The Langham, Boston
4.5 out of 5.0Mon, Jul 23 - Sun, Jul 29
CHI-All Airports - Logan Intl.
$1,279 per person
Hampton Inn Boston - Norwood
3.0 out of 5.0Mon, Jul 23 - Sun, Jul 29
CHI-All Airports - Logan Intl.
$797 per person
The Ritz-Carlton, Boston
5.0 out of 5.0Mon, Jul 23 - Sun, Jul 29
CHI-All Airports - Logan Intl.
$1,827 per person
Aloft Lexington
3.0 out of 5.0Mon, Jul 23 - Sun, Jul 29
CHI-All Airports - Logan Intl.
$619 per person
Extended Stay America Boston - Braintree
2.5 out of 5.0Mon, Jul 23 - Sun, Jul 29
CHI-All Airports - Logan Intl.
$653 per person
More to explore for Chicago to Boston
Explore Boston with Orbitz's Travel Guides to find the best flights, cars, vacation packages and more!
Airports near Chicago
Airports near Boston
Flights from Cities near Chicago
Flights to Cities near Boston
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- Minneapolis - St. Paul to Boston
- Denver to Boston
- Seattle to Boston
- Houston to Boston
- Dallas to Boston
- Baltimore to Boston
- Orlando to Boston
- Atlanta to Boston
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Top Hotels in Boston
- Revere Hotel Boston Common
- The Godfrey Hotel Boston
- Boston Omni Parker House Hotel
- Lakeside Inn
- Boston Park Plaza
- Sheraton Boston Hotel
- Archer Hotel Burlington
- Hampton Inn Boston Waltham
- Hyatt Place Boston/Braintree
- The Bostonian Boston
- Copley Square Hotel
- Boston Marriott Copley Place
- Copley House
- Royal Sonesta Boston
- HYATT house Boston/Burlington
- Hilton Boston Logan Airport
- SpringHill Suites by Marriott Boston Peabody
- HYATT house Boston/Waltham
- Red Roof Inn PLUS+ Boston - Logan
- The Lenox Hotel Boston
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.
*Savings based on all holiday package bookings with Flight + Hotel on Orbitz.com from January through December 2017, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.