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Flight Deals from Chicago O Hare Airport to Boston from $58

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Stops

  • Nonstop
    from $116
  • Up to 1 stop
    $164

Airlines

  • American Airlines
    $186
  • Delta Air Lines
    $116
  • JetBlue
    $151
  • Spirit Airlines
    $166
  • United Airlines
    $186

Cabin Class

  • Economy
    $116

Departure Airports

  • Chicago O Hare Airport
    $116

Arrival Airports

  • General Edward Lawrence Logan International Airport
    $116

Layover Airports

  • Detroit Metropolitan Airport
    $216
  • Fort Lauderdale Hollywood International Airport
    $166
  • Myrtle Beach International Airport
    $213
  • New York John F Kennedy Airport
    $164
  • New York LaGuardia Airport
    $216
  • Newark Liberty Airport
    $236
  • Orlando International Airport
    $166
  • Reagan Washington National Airport
    $253
  • Washington Dulles Airport
    $236

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Delta Air Lines Logo
Delta Air Lines

09/08/25

ORD
3h 34m
Direct

09/08/25

BOS
Delta Air Lines Logo
Delta Air Lines

09/09/25

BOS
1h 55m
Direct

09/09/25

ORD
$116
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

09/16/25

ORD
3h 32m
Direct

09/16/25

BOS
Delta Air Lines Logo
Delta Air Lines

09/24/25

BOS
1h 52m
Direct

09/24/25

ORD
$116
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

09/27/25

ORD
3h 37m
Direct

09/27/25

BOS
Delta Air Lines Logo
Delta Air Lines

10/01/25

BOS
1h 52m
Direct

10/01/25

ORD
$136
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

09/19/25

ORD
3h 34m
Direct

09/19/25

BOS
JetBlue Logo
JetBlue

09/21/25

BOS
1h 54m
Direct

09/21/25

ORD
$151
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

09/26/25

ORD
7h 22m
JFK

09/26/25

BOS
JetBlue Logo
JetBlue

10/01/25

BOS
1h 54m
Direct

10/01/25

ORD
$164
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

09/19/25

ORD
7h 44m
JFK

09/19/25

BOS
JetBlue Logo
JetBlue

09/21/25

BOS
1h 54m
Direct

09/21/25

ORD
$164
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

09/17/25

ORD
8h 20m
MCO

09/17/25

BOS
Spirit Airlines Logo
Spirit Airlines

09/20/25

BOS
11h 27m
FLL

09/20/25

ORD
$166
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

09/16/25

ORD
3h 31m
Direct

09/16/25

BOS
United Airlines Logo
United Airlines

09/24/25

BOS
1h 50m
Direct

09/24/25

ORD
$186
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

09/07/25

ORD
3h 24m
Direct

09/07/25

BOS
American Airlines Logo
American Airlines

09/09/25

BOS
2h 7m
Direct

09/09/25

ORD
$186
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

09/19/25

ORD
3h 30m
Direct

09/20/25

BOS
United Airlines Logo
United Airlines

09/25/25

BOS
1h 50m
Direct

09/25/25

ORD
$186
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

09/28/25

ORD
3h 24m
Direct

09/28/25

BOS
American Airlines Logo
American Airlines

10/02/25

BOS
1h 58m
Direct

10/02/25

ORD
$186
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

09/21/25

ORD
3h 30m
Direct

09/22/25

BOS
United Airlines Logo
United Airlines

09/25/25

BOS
1h 56m
Direct

09/25/25

ORD
$186
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

09/12/25

ORD
3h 44m
Direct

09/13/25

BOS
American Airlines Logo
American Airlines

09/14/25

BOS
1h 58m
Direct

09/14/25

ORD
$186
Free cancellation within 83 hours of booking
JetBlue Logo
JetBlue

09/19/25

ORD
5h 42m
JFK

09/19/25

BOS
JetBlue Logo
JetBlue

09/21/25

BOS
6h 9m
JFK

09/21/25

ORD
$212
Free cancellation within 83 hours of booking
Spirit Airlines Logo
Spirit Airlines

09/13/25

ORD
9h 10m
FLL

09/14/25

BOS
Spirit Airlines Logo
Spirit Airlines

09/15/25

BOS
7h 44m
MYR

09/15/25

ORD
$213
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

09/21/25

ORD
6h 52m
LGA

09/21/25

BOS
Delta Air Lines Logo
Delta Air Lines

09/25/25

BOS
1h 52m
Direct

09/25/25

ORD
$216
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

09/17/25

ORD
3h 34m
Direct

09/17/25

BOS
Delta Air Lines Logo
Delta Air Lines

09/21/25

BOS
4h 30m
LGA

09/21/25

ORD
$216
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

09/08/25

ORD
5h 30m
LGA

09/08/25

BOS
Delta Air Lines Logo
Delta Air Lines

09/09/25

BOS
1h 55m
Direct

09/09/25

ORD
$216
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

09/24/25

ORD
3h 32m
Direct

09/24/25

BOS
Delta Air Lines Logo
Delta Air Lines

09/28/25

BOS
3h 20m
DTW

09/28/25

ORD
$216
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

09/30/25

ORD
3h 37m
Direct

09/30/25

BOS
Delta Air Lines Logo
Delta Air Lines

10/08/25

BOS
4h
DTW

10/08/25

ORD
$216
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

09/27/25

ORD
3h 30m
Direct

09/27/25

BOS
Delta Air Lines Logo
Delta Air Lines

10/01/25

BOS
3h 22m
DTW

10/01/25

ORD
$236
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

10/02/25

ORD
3h 30m
Direct

10/03/25

BOS
United Airlines Logo
United Airlines

10/05/25

BOS
4h 6m
IAD

10/05/25

ORD
$236
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

09/21/25

ORD
8h 14m
EWR

09/21/25

BOS
United Airlines Logo
United Airlines

09/25/25

BOS
1h 56m
Direct

09/25/25

ORD
$236
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

09/12/25

ORD
3h 31m
Direct

09/12/25

BOS
United Airlines Logo
United Airlines

09/14/25

BOS
4h 29m
EWR

09/14/25

ORD
$236
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

09/24/25

ORD
3h 35m
Direct

09/24/25

BOS
United Airlines Logo
United Airlines

09/28/25

BOS
4h 6m
IAD

09/28/25

ORD
$236
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

09/19/25

ORD
5h 23m
EWR

09/19/25

BOS
United Airlines Logo
United Airlines

09/22/25

BOS
1h 54m
Direct

09/22/25

ORD
$236
Free cancellation within 83 hours of booking
United Airlines Logo
United Airlines

09/07/25

ORD
3h 26m
Direct

09/07/25

BOS
United Airlines Logo
United Airlines

09/09/25

BOS
5h 8m
IAD

09/09/25

ORD
$236
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

09/30/25

ORD
3h 38m
Direct

09/30/25

BOS
American Airlines Logo
American Airlines

10/08/25

BOS
4h 24m
DCA

10/08/25

ORD
$253
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

09/17/25

ORD
6h 53m
DCA

09/17/25

BOS
American Airlines Logo
American Airlines

09/21/25

BOS
1h 58m
Direct

09/21/25

ORD
$253
Free cancellation within 83 hours of booking
American Airlines Logo
American Airlines

09/24/25

ORD
6h 58m
DCA

09/24/25

BOS
American Airlines Logo
American Airlines

09/28/25

BOS
1h 58m
Direct

09/28/25

ORD
$253
Free cancellation within 83 hours of booking

Top Deals on flights from Chicago O Hare Airport to Boston

Chicago, US (CHI) - Boston, US (BOS)

JetBlue Logo
JetBlue

Jun 6

ORD
3h 29m
Direct

Jun 6

BOS

as low as

$58

Chicago, US (CHI) - Boston, US (BOS)

United Airlines Logo
United Airlines

May 29

ORD
3h 29m
Direct

May 30

BOS

as low as

$58

Chicago, US (CHI) - Boston, US (BOS)

Delta Air Lines Logo
Delta Air Lines

Jun 12

ORD
3h 31m
Direct

Jun 12

BOS

as low as

$58

Chicago, US (CHI) - Boston, US (BOS)

Spirit Airlines Logo
Spirit Airlines

Jun 10

ORD
10h 48m
FLL

Jun 10

BOS

as low as

$69

Chicago, US (CHI) - Boston, US (BOS)

Spirit Airlines Logo
Spirit Airlines

Jun 4

ORD
14h 13m
MCO

Jun 4

BOS

as low as

$75

Chicago, US (CHI) - Boston, US (BOS)

JetBlue Logo
JetBlue

May 28

ORD
7h 59m
JFK

May 28

BOS

as low as

$92

Chicago, US (CHI) - Boston, US (BOS)

American Airlines Logo
American Airlines

May 21

ORD
3h 26m
Direct

May 21

BOS

as low as

$93

Chicago, US (CHI) - Boston, US (BOS)

 Logo

May 29

ORD
3h 29m
Direct

May 30

BOS

as low as

$97

Chicago, US (CHI) - Boston, US (BOS)

United Airlines Logo
United Airlines

May 29

ORD
7h 28m
EWR

May 29

BOS

as low as

$98

Chicago, US (CHI) - Boston, US (BOS)

 Logo

May 17

ORD
8h 29m
MCO

May 18

BOS

as low as

$103

Chicago, US (CHI) - Boston, US (BOS)

Spirit Airlines Logo
Spirit Airlines

Jun 13

ORD
6h 5m
MYR

Jun 13

BOS

as low as

$116

Chicago, US (CHI) - Boston, US (BOS)

American Airlines Logo
American Airlines

May 29

ORD
7h 47m
PHL

May 29

BOS

as low as

$123

Frequently Asked Questions

What is the typical flight duration from Chicago O Hare Airport to Boston?
The typical flight duration between Chicago O Hare Airport and Boston lasts between 2.5 to 3.5 hours. This estimate covers direct flights, though variations may occur due to weather conditions and flight schedules. Travelers can expect a comfortable experience with onboard conveniences that enhance the journey. It is advisable to check your flight details a few weeks in advance since minor delays could extend travel time. This practical insight helps in planning your departure from Chicago and arrival in Boston with manageable layover expectations.
Are there any direct flights from Chicago O Hare Airport to Boston?
Yes, there are direct flights available from Chicago O Hare Airport to Boston, offering nonstop travel that lasts between 2.5 to 3.5 hours. These flights provide a seamless and time-efficient experience. However, availability can vary by season and airline schedules, so it is a good idea to book early. Direct flights tend to be more reliable and often feature additional comfort options onboard. This is helpful for travelers seeking a quick transition from Chicago to Boston without the hassle of stopovers.
What are the best transportation options from Boston Logan Airport to downtown?
For those arriving at Boston Logan Airport, there are several efficient transportation options to downtown. You can choose taxis or rideshares which generally cost between $20 to $40, or opt for the MBTA subway with fares around $2.75 per ride. Shuttle services are also popular and accommodate luggage, ensuring comfort and convenience. Each mode has its advantages based on your budget and time constraints, providing a smooth connection from the airport to the heart of Boston for travelers coming from Chicago.
What are the must-see attractions in Boston for travelers arriving from Chicago O Hare Airport?
Travelers arriving from Chicago O Hare Airport visiting Boston should definitely explore iconic attractions such as the Freedom Trail, Faneuil Hall, and Boston Common. These sites offer a glimpse into the city’s rich historical and cultural tapestry. Additionally, experiences like visiting the Paul Revere House and the Museum of Fine Arts provide deep insights into local heritage. Exploring vibrant neighborhoods suitable for leisurely walks can also enrich your visit. Taking advantage of guided tours may offer further context, ensuring a memorable trip with practical insights into Boston’s legacy.
Which local dishes should travelers from Chicago O Hare Airport try when visiting Boston?
Travelers from Chicago O Hare Airport should sample traditional New England cuisine when in Boston. Don’t miss the opportunity to try New England clam chowder, lobster rolls, and baked beans, each reflecting the coastal flavors and heritage of the region. These dishes vary in price, typically ranging from $15 to $40 per serving, depending on the restaurant. Exploring local seafood eateries or popular food markets can provide a well-rounded taste of these specialties. This culinary experience is both authentic and delicious, ensuring a true taste of Boston’s cultural identity.
Are there any budget-friendly hotels in Boston for visitors from Chicago O Hare Airport?
Yes, Boston offers a variety of budget-friendly hotel options that cater to visitors from Chicago O Hare Airport. You can find accommodations ranging from $100 to $200 per night in neighborhoods with easy access to downtown attractions and public transportation. Options include well-regarded chain hotels as well as charming boutique inns. It’s beneficial to compare different booking websites or consider package deals for the best rates. Early reservations are encouraged, especially during peak travel times, to secure both the best prices and convenient locations within the city.
What are the best family-friendly activities in Boston for travelers from Chicago O Hare Airport?
Travelers from Chicago O Hare Airport planning a family trip to Boston will find a wide range of activities suited for all ages. Popular attractions include the Boston Children’s Museum, New England Aquarium, and Franklin Park Zoo, where admission generally ranges from $15 to $35 per person. Additionally, a walk along the historic Freedom Trail offers an engaging yet educational outing. These destinations combine fun and learning in a vibrant setting. With plenty of interactive exhibits and outdoor spaces, families are assured a memorable visit that balances both cultural enrichment and recreation.
Is there a specific time of year when Boston is best visited by travelers from Chicago O Hare Airport?
Yes, the ideal period to visit generally falls between late spring and early fall, from May to September. During this time, Boston experiences mild weather that is perfect for outdoor activities and sightseeing. This period also boasts a vibrant events calendar including festivals and cultural celebrations. Travelers from Chicago O Hare Airport will benefit from extended daylight hours and a lively urban atmosphere that enhances sightseeing. Booking during these months offers a good balance between enjoying the pleasant outdoor environment and taking advantage of various seasonal events hosted throughout the city.
What are the top cultural experiences in Boston that travelers from Chicago O Hare Airport should not miss?
Travelers arriving from Chicago O Hare Airport are encouraged to dive into Boston’s rich cultural scene by visiting institutions like the Museum of Fine Arts and the Isabella Stewart Gardner Museum. Exploring the historic Freedom Trail provides another cultural narrative, connecting you with pivotal moments in American history. Additionally, local theaters, art galleries, and cultural festivals add to the immersive experience. These venues, with ticket prices ranging from $10 to $40, deliver valuable insights into the city’s artistic and historical heritage, ensuring an enriching journey full of local charm and educational opportunities.
What are the customs requirements for travelers flying from Chicago O Hare Airport to Boston?
Since travels between Chicago O Hare Airport and Boston are domestic, customs requirements are minimal. Travelers need only a valid, government-issued photo ID, such as a driver’s license or passport, to pass through security. It remains advisable to review Transportation Security Administration guidelines before departure to account for any changes. In domestic flights like these, the process is streamlined, focusing on security checks rather than customs formalities. Ensuring all identification is current and arriving at the airport early contributes to a smooth experience as you transition from Chicago to Boston.
Are there any seasonal events in Boston that travelers from Chicago O Hare Airport should not miss?
Yes, Boston hosts several seasonal events that offer rich cultural engagements. Noteworthy events include the Boston Marathon in April, Fourth of July celebrations, and various fall festivals showcasing local art, food, and history. These events provide immersive experiences, allowing travelers to enjoy parades, community gatherings, and local performances. Tickets for some events may cost between $10 to $30, while others are free to attend. It is advisable to check event schedules close to your travel dates to plan accordingly, ensuring you capture the vibrancy of Boston’s cultural calendar.
What are the best places to shop for souvenirs in Boston for travelers from Chicago O Hare Airport?
Travelers from Chicago O Hare Airport visiting Boston will find excellent souvenir shopping options in bustling districts. Faneuil Hall Marketplace and Newbury Street are well-known for offering locally crafted items, unique artwork, and historical memorabilia. Prices in these areas range from approximately $10 for small trinkets to $100 or more for high-quality artisan pieces. These shopping destinations not only provide diverse products but also immerse you in the city's lively atmosphere. It is advisable to allocate extra time to explore these markets and discover unique items that reflect Boston’s rich heritage.
What health precautions should travelers from Chicago O Hare Airport take when visiting Boston?
Travelers from Chicago O Hare Airport visiting Boston should adopt standard health precautions typical for major cities. This includes carrying travel insurance, keeping any necessary medications on hand, and staying updated with local health advisories. Frequently washing hands and using hand sanitizer is recommended, particularly in crowded areas. It is also wise to verify if seasonal vaccinations, such as the flu shot, are advised during your visit. Familiarize yourself with emergency contacts and nearby medical facilities. These proactive measures help ensure a safe and enjoyable experience in Boston.
What unique airport amenities can travelers expect at Boston Logan Airport?
Travelers arriving at Boston Logan Airport can expect a range of amenities designed to enhance comfort and convenience. The airport offers diverse dining options, retail outlets, and comfortable lounges with prices for food and drinks ranging from $5 to $50. Free Wi-Fi access, charging stations, and clear signage add to the seamless experience. Relaxation areas and baggage assistance services further mitigate the typical travel stress. These features collectively ensure that those arriving from Chicago O Hare Airport have a practical and pleasant transition through Boston’s airport, setting the tone for a great visit.
Are there any special services available for travelers with pets at Boston Logan Airport?
Yes, Boston Logan Airport provides several pet-friendly services that ease travel concerns for pet owners. Special amenities include designated pet relief areas, pet-friendly waiting zones, and sometimes even assistance with handling and boarding procedures. Costs for these services generally range from $10 to $30 depending on the specific requirements. It is advisable for pet travelers from Chicago O Hare Airport to contact their airline in advance to confirm all pet policies and necessary documentation. This proactive step ensures that both you and your pet have a comfortable and seamless experience while transiting through the airport.
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