$55 Cheap flight deals from Chicago (CHI) to Boston (BOS)

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This Weekend's Flight Deals from Chicago to Boston

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, May 2 - Sun, May 4
ORD
O'Hare Intl.
BOS
Logan Intl.
$155 Roundtrip, just found
$155
Roundtrip
just found
Select JetBlue Airways flight, departing Fri, May 2 from O'Hare Intl. to Logan Intl., returning Sun, May 4, priced at $155 just found
Fri, May 2 - Sun, May 4
MDW
Midway Intl.
BOS
Logan Intl.
$190 Roundtrip, found 22 hours ago
$190
Roundtrip
found 22 hours ago
Select Frontier Airlines flight, departing Fri, May 2 from Midway Intl. to Logan Intl., returning Sun, May 4, priced at $190 found 22 hours ago
Fri, May 2 - Mon, May 5
ORD
O'Hare Intl.
ORH
Worcester Regional
$226 Roundtrip, found 7 hours ago
$226
Roundtrip
found 7 hours ago
Select American Airlines flight, departing Fri, May 2 from O'Hare Intl. to Worcester Regional, returning Mon, May 5, priced at $226 found 7 hours ago
Sat, May 3 - Tue, May 20
ORD
O'Hare Intl.
MHT
Manchester-Boston Regional
$468 Roundtrip, found 6 days ago
$468
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, May 3 from O'Hare Intl. to Manchester-Boston Regional, returning Tue, May 20, priced at $468 found 6 days ago

Airfares from $55 One Way, $109 Round Trip from Chicago to Boston

Prices starting at $109 for return flights and $55 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.

Tue, May 20 - Wed, May 21
ORD
Chicago
BOS
Boston
$109 Roundtrip, found 14 hours ago
$109
Roundtrip
found 14 hours ago
Select JetBlue Airways flight, departing Tue, May 20 from Chicago to Boston, returning Wed, May 21, priced at $109 found 14 hours ago
Thu, Oct 23 - Thu, Oct 30
ORD
Chicago
BOS
Boston
$109 Roundtrip, found 1 day ago
$109
Roundtrip
found 1 day ago
Select Spirit Airlines flight, departing Thu, Oct 23 from Chicago to Boston, returning Thu, Oct 30, priced at $109 found 1 day ago
Sun, Jun 8 - Sat, Jun 14
MDW
Chicago
BOS
Boston
$117 Roundtrip, found 2 days ago
$117
Roundtrip
found 2 days ago
Select Southwest Airlines flight, departing Sun, Jun 8 from Chicago to Boston, returning Sat, Jun 14, priced at $117 found 2 days ago
Wed, Jul 9 - Wed, Jul 16
ORD
Chicago
ORH
Worcester
$186 Roundtrip, found 14 hours ago
$186
Roundtrip
found 14 hours ago
Select American Airlines flight, departing Wed, Jul 9 from Chicago to Worcester, returning Wed, Jul 16, priced at $186 found 14 hours ago
Tue, May 20 - Wed, May 28
ORD
Chicago
PVD
Providence
$217 Roundtrip, found 16 hours ago
$217
Roundtrip
found 16 hours ago
Select JetBlue Airways flight, departing Tue, May 20 from Chicago to Providence, returning Wed, May 28, priced at $217 found 16 hours ago

Boston economy flight packages

Price found within the past 48 hours. Click for updated prices.
Quality Inn Chicopee - Springfield
2.5-star property

Quality Inn Chicopee - Springfield

6.6/10 (676 reviews)

Jun 19 - Jun 24

5 night stay

Chicago (ORD) to Boston (BOS)

United • Roundtrip • Coach
per person
found 1 day ago
Room is ok, didn’t like the outside look. Staff is friendly.

Reviewed on Jul 18, 2022

The Beverly
3.0-star property

The Beverly

8.4/10 Very Good! (277 reviews)

Jun 18 - Jun 21

3 night stay

Chicago (ORD) to Boston (BOS)

Spirit Airlines • Non-stop • Coach

Boston (BOS) to Chicago (ORD)

American Airlines • Non-stop • Coach
Save 100% on your flight
per person
found 1 day ago
Expecting a modern, well-maintained hotel as depicted in their online photos. Unfortunately, it was clearly a motel, and this misleading information set unrealistic expectations for my stay. Despite being a non-smoking establishment, my room reeked of cigarette smoke and had a pervasive musty smell, making the stay very uncomfortable. The carpet was filthy, and the throw pillows were dirty and smelly, looking like they hadn’t been washed or replaced in years. The vent next to the bathroom sink was covered in a thick layer of dust, indicating a lack of proper cleaning and maintenance. The overall condition of the room was poor, with subpar cleanliness and unacceptable air quality due to the strong odors. There is no staff on-site, so you have to text them for assistance. When I texted about the awful smell, I received a response after 15 minutes: “I am so sorry to hear that. I am looking into the situation now and will get right back to you.” As we had been driving all day and were starving, I responded that we were heading out to eat and would deal with it when we returned. They never responded to that message. Upon returning from dinner, we struggled to fall asleep due to the thin walls. We could hear conversations from all neighboring rooms, including those above us, and any movement they made was very loud. Overall, was very disappointed with my stay and would not recommend this place to anyone looking for comfortable and clean accommodation.

Reviewed on Jul 28, 2024

Motel 6 Chicopee, MA - Springfield
2.0-star property

Motel 6 Chicopee, MA - Springfield

6.4/10 (1,001 reviews)

Jun 19 - Jun 24

5 night stay

Chicago (ORD) to Boston (BOS)

United • Roundtrip • Coach
per person
found 1 day ago
Great hotel for the value.

Reviewed on Nov 3, 2024

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Boston first class flight packages

Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel
3.5-star property

The Revolution Hotel

8.8/10 Excellent! (1,968 reviews)

May 29 - Jun 3

5 night stay

Chicago (CHI) to Boston (BOS)

Delta • FirstClass

Boston (BOS) to Chicago (CHI)

American Airlines • FirstClass
per person
found 7 hours ago
Stayed in King Room with shared bathroom down hall. Bathrooms were clean. Adequate towels were available. Staff were super friendly and helpful.

Reviewed on Oct 11, 2024

Meco Hotel
2.0-star property

Meco Hotel

8.4/10 Very Good! (118 reviews)

May 29 - Jun 3

5 night stay

Chicago (CHI) to Boston (BOS)

Delta • FirstClass

Boston (BOS) to Chicago (CHI)

American Airlines • FirstClass
Save 100% on your flight
per person
found 7 hours ago
Loved it, thank you Meco Hotel!

Reviewed on Mar 29, 2025

YOTEL Boston
4.0-star property

YOTEL Boston

8.6/10 Excellent! (1,978 reviews)

May 29 - Jun 3

5 night stay

Chicago (CHI) to Boston (BOS)

Delta • FirstClass

Boston (BOS) to Chicago (CHI)

American Airlines • FirstClass
per person
found 7 hours ago
Convenient. Clean. Close to shops and restaurants in the seaport.

Reviewed on Jan 29, 2025

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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
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

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.

Frequently asked questions

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
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 Orbitz.com 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.