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Flight Deals from Chicago 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 Midway Airport
    $216
  • 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

09/16/25

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

09/08/25

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

09/27/25

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
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

09/26/25

ORD
3h 30m
Direct

09/27/25

BOS
United Airlines Logo
United Airlines

10/01/25

BOS
1h 50m
Direct

10/01/25

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

09/08/25

ORD
3h 30m
Direct

09/09/25

BOS
United Airlines Logo
United Airlines

09/09/25

BOS
1h 56m
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

09/22/25

BOS
1h 54m
Direct

09/22/25

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

09/17/25

ORD
3h 38m
Direct

09/17/25

BOS
American Airlines Logo
American Airlines

09/21/25

BOS
1h 58m
Direct

09/21/25

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

09/22/25

ORD
3h 44m
Direct

09/23/25

BOS
American Airlines Logo
American Airlines

09/29/25

BOS
1h 59m
Direct

09/29/25

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

09/17/25

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

09/21/25

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

09/16/25

ORD
3h 37m
Direct

09/16/25

BOS
Delta Air Lines Logo
Delta Air Lines

09/24/25

BOS
5h 41m
DTW

09/24/25

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

09/08/25

MDW
5h 35m
DTW

09/08/25

BOS
Delta Air Lines Logo
Delta Air Lines

09/09/25

BOS
1h 55m
Direct

09/09/25

MDW
$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
United Airlines Logo
United Airlines

09/19/25

ORD
3h 31m
Direct

09/19/25

BOS
United Airlines Logo
United Airlines

09/22/25

BOS
4h 38m
EWR

09/22/25

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

09/25/25

ORD
6h 14m
EWR

09/25/25

BOS
United Airlines Logo
United Airlines

09/29/25

BOS
1h 50m
Direct

09/29/25

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

09/21/25

ORD
3h 31m
Direct

09/21/25

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

09/22/25

ORD
6h 5m
IAD

09/22/25

BOS
United Airlines Logo
United Airlines

09/29/25

BOS
1h 56m
Direct

09/29/25

ORD
$236
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

09/19/25

MDW
5h 35m
DTW

09/19/25

BOS
Delta Air Lines Logo
Delta Air Lines

09/25/25

BOS
1h 52m
Direct

09/25/25

MDW
$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

09/17/25

ORD
3h 31m
Direct

09/17/25

BOS
United Airlines Logo
United Airlines

09/21/25

BOS
4h 29m
EWR

09/21/25

ORD
$236
Free cancellation within 83 hours of booking
Delta Air Lines Logo
Delta Air Lines

09/28/25

ORD
6h 52m
LGA

09/28/25

BOS
Delta Air Lines Logo
Delta Air Lines

10/02/25

BOS
1h 52m
Direct

10/02/25

ORD
$245
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

Top Deals on flights from Chicago 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)

Delta Air Lines Logo
Delta Air Lines

Jun 4

ORD
3h 32m
Direct

Jun 4

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)

Spirit Airlines Logo
Spirit Airlines

Jun 11

ORD
10h 48m
FLL

Jun 11

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 20

ORD
8h 14m
JFK

May 21

BOS

as low as

$92

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

American Airlines Logo
American Airlines

Jun 10

ORD
3h 19m
Direct

Jun 10

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)

 Logo

Jun 1

MDW
11h 23m
MCO

Jun 2

BOS

as low as

$119

Frequently Asked Questions

What is the typical flight duration from Chicago to Boston?
Direct flights between Chicago and Boston typically take between 2 to 3 hours, depending on weather conditions and air traffic. This relatively short – yet comfortable – duration makes it a popular route for business and leisure travelers. While variations in departure times may slightly affect the total travel time, most flights maintain a quick turnaround, offering timely arrivals. Travelers are advised to check in advance for any potential delays and to choose flights that best meet their schedule requirements.
Are there any direct flights available from Chicago to Boston?
Yes, there are direct flights available between Chicago and Boston. Major airlines operate daily direct services, making this route convenient for both business and leisure visitors. Flight durations are usually between 2 to 3 hours. Ticket prices can range from $150 to $300, depending on the time of booking and seasonal demand. It is advisable to check multiple travel platforms for the most competitive rates and to book early during peak travel periods to secure a direct and comfortable flight.
What are the best transportation options from Boston Logan International Airport to downtown Boston?
The top transportation options include the Silver Line bus, taxis, rideshares, and car rentals. The Silver Line is an excellent economy choice with a fare that ranges from free to around $2 depending on your exact route, offering direct access to downtown areas. Alternatively, taxis and rideshares cost between $20 to $40, providing convenience for those with heavy luggage. For a more independent experience, rental cars are available with varying daily rates. Reviewing real-time transit updates and comparing prices ahead of time can improve your overall travel experience.
What are the must-see attractions in Boston for travelers arriving from Chicago?
Travelers should explore top attractions like the Freedom Trail, Boston Common, and the New England Aquarium. These sites offer a blend of historical insights and modern entertainment. Additionally, Faneuil Hall and Quincy Market present opportunities to experience vibrant local culture and cuisine. For a well-rounded visit, it is recommended to participate in a guided tour to fully appreciate the rich history and architectural beauty. Each attraction typically offers unique experiences, making your time in Boston both memorable and enriching.
Which local dishes should travelers from Chicago try when visiting Boston?
Travelers should sample New England’s unique culinary offerings including clam chowder, lobster rolls, baked beans, and Boston cream pie. These dishes are readily available at local seafood shacks, neighborhood diners, and dedicated food markets. Prices per dish can range from $15 to $40 depending on the dining venue. For an authentic experience, consider dining near Quincy Market or joining a food tour that highlights local specialties. Each of these dishes provides a taste of Boston’s rich regional heritage and offers a welcome change for visitors from Chicago.
What are the best family-friendly activities in Boston for visitors from Chicago?
Family-friendly activities include exploring the New England Aquarium, visiting the interactive exhibits at the Boston Children’s Museum, and enjoying outdoor time at the Boston Public Garden. Other recommended outings include strolling along the Freedom Trail and visiting local parks where children can run and play. Admission prices typically range from $15 to $30 per person. It’s smart to plan weekday visits to avoid the peak crowds while ensuring a fun and educational experience for all family members as you explore local history and culture.
What are the most affordable dining options in Boston for travelers from Chicago?
For budget-conscious visitors, affordable dining options include food trucks, casual cafes, and local diners where meals can cost between $10 to $20. Areas such as the North End and Chinatown offer reasonably priced meals with authentic flavors. Street vendors and quick-serve restaurants also provide hearty options without compromising on taste. Planning your dining schedule during off-peak hours may also yield discounts. Checking recent local reviews online helps verify current prices and quality, ensuring you make the best culinary choices during your stay.
Are there any cultural festivals in Boston that travelers from Chicago should not miss?
Yes, Boston hosts several cultural festivals that are not to be missed. Events like the Boston Calling Music Festival and local heritage celebrations highlight diverse musical acts, art installations, and traditional foods. These festivals, usually held during the summer and early fall, offer exciting local experiences with ticket prices ranging from free entry to about $50. They provide an immersive cultural insight into Boston’s rich community traditions. Checking local event calendars ahead of your trip can help you plan your visit to coincide with these vibrant festivities.
What are the best shopping areas in Boston for souvenirs for travelers from Chicago?
For memorable souvenirs, explore Quincy Market, Faneuil Hall Marketplace, and Newbury Street. These locations offer a mix of local crafts, clothing, and collectibles that echo Boston’s historical and cultural vibe. Prices for souvenirs can vary, typically falling between $10 to $100, which suits varied budgets. For unique finds, consider stopping by smaller boutique shops that offer locally handcrafted items. These shopping areas not only offer great deals but also provide an atmosphere filled with local heritage, making your souvenir hunt both fun and productive.
What safety tips should travelers from Chicago keep in mind while visiting Boston?
Travelers should practice standard safety measures such as keeping valuables secure in crowded areas like downtown markets and historic trails. Use well-lit streets after dark and opt for trusted transport providers such as licensed taxis or rideshares. It is wise to familiarize yourself with local emergency numbers and monitor weather-related advisories. Additionally, keep digital copies of personal identification and important documents. Staying informed through local news outlets and following the advice of local authorities can also ensure a safe and worry-free visit.
What are the best seating options for families traveling from Chicago to Boston?
Airlines typically offer family seating options that include bulkhead seats for extra legroom and easier access to facilities designed for young children. These options often come as part of the booking process and can range in availability from complimentary choices to reserved selections with minor fees. For comfort during flights, inquire at the time of booking to ensure seating preferences are met. In attractions or events at your destination, designated family seating areas further enhance convenience, guaranteeing that your travel experience is comfortable and accommodating for all family members.
Is there a specific time of year when Boston is best visited by travelers from Chicago?
Yes, the optimal time to visit is during the spring and fall, when Boston experiences mild weather and fewer crowds. These seasons feature comfortable temperatures ranging from 55°F to 70°F, perfect for exploring historical sites and local neighborhoods. Visitors can enjoy outdoor tours, cultural events, and scenic walks without the discomfort of extreme weather. Planning your itinerary during these periods not only improves your sightseeing experience but also provides opportunities to partake in seasonal festivals and events unique to the city.
What health precautions should travelers from Chicago consider before flying to Boston?
Travelers should ensure that routine immunizations are up-to-date and consider a seasonal flu shot, especially during the cold months. Carrying a small medical kit, including hand sanitizer, masks, and any personal prescription medications, is advisable. Staying hydrated during the flight and maintaining good hand hygiene can help prevent illness. It is also beneficial to review current health advisories and, if needed, talk with a healthcare provider prior to travel. Finally, appropriate travel insurance covering health emergencies adds an extra layer of precaution.
What unique airport amenities can travelers expect at Boston Logan International Airport?
At Boston Logan International Airport, travelers can access a range of unique amenities including a variety of dining options, comfortable lounges, free Wi-Fi, and retail stores. Families benefit from designated play areas and kid-friendly zones, while business travelers enjoy working spaces with charging stations. Additional services such as currency exchange, spa treatments, and art exhibits enhance the airport experience. Prices or fees for certain services can vary from complimentary access with your ticket to ranges between $5 and $30 for services like spa treatments. Exploring the airport layout prior to arrival may improve convenience.
What are the customs requirements for travelers flying from Chicago to Boston?
This information is not applicable to Boston or Chicago because both cities are in the United States and domestic flights do not require customs clearance. Travelers only need to present acceptable identification, such as a state-issued ID or driver’s license, in accordance with TSA regulations. It is always a good practice to verify any updated security guidelines before departure. Arriving early at the airport allows time for security screenings. Following these domestic travel protocols will ensure a smooth, hassle-free journey.
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