---
title: "Chicago to Boston cheap flights from $116 (CHI to BOS) - Expedia"
description: "Compare cheap Flights from Chicago (CHI) to Boston (BOS) start at $116 for one-way and $220 for round trip. Earn your airline miles on top of our rewards!"
canonical: "https://www.expedia.com/lp/flights/chi/bos/chicago-to-boston"
language: en-US
market: US
currency: USD
prices_as_of: 2026-11-14T00:41:21Z
---

# $116 Cheap Flights from Chicago (CHI) to Boston (BOS)
![A city street with a historic building labeled 'QUINCY MARKET,' trees with autumn leaves, and modern high-rise buildings.](https://images.trvl-media.com/place/5459778/1efe54a0-5011-4269-b6c4-92db64d64036.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

[View $116 flight on Sat, Dec 19, 2026](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:BOS,departure:12/19/2026TANYT&trip=oneway&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:115.59&airProductToken=AQpgCi4IxnISBDE0NTgY7LABIMxwKJuhoAMwxaKgAzhSQABYAWoDRUNPcgdSMjFPWFA0Ci4IxnISBDMzNDgYzHAgwZMBKK2loAMw5qagAzhSQAFYAWoDRUNPcgdSMjFPWFA0EgoIARABGAEqAkY5GAEiBAgBEAEoAigDKAQwAQ)

## Popular airlines from Chicago to Boston, MA (BOS-Logan Intl.)

[JetBlue Airways](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:BOS,departure:11/28/2026TANYT&leg2=from:BOS,to:CHI,departure:12/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"B6"}}])

[Delta](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:BOS,departure:11/28/2026TANYT&leg2=from:BOS,to:CHI,departure:12/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"DL"}}])

[American Airlines](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:BOS,departure:11/28/2026TANYT&leg2=from:BOS,to:CHI,departure:12/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AA"}}])

[United](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:BOS,departure:11/28/2026TANYT&leg2=from:BOS,to:CHI,departure:12/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"UA"}}])

[Alaska Airlines](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:BOS,departure:11/28/2026TANYT&leg2=from:BOS,to:CHI,departure:12/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"AS"}}])

[Frontier Airlines](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:BOS,departure:11/28/2026TANYT&leg2=from:BOS,to:CHI,departure:12/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"F9"}}])

[Southwest Airlines](https://www.expedia.com/Flights-Search?leg1=from:CHI,to:BOS,departure:11/28/2026TANYT&leg2=from:BOS,to:CHI,departure:12/5/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&filters=[{"preferredAirlineFilterValue":{"carrierCode":"WN"}}])

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## Cheap Flights from Chicago to Boston (CHI-BOS)

Prices were available within the past 7 days and start at $116 for one-way flights and $220 for roundtrip, for the period specified. Prices and availability are subject to change.

All deals

One way

Roundtrip

[Select Frontier Airlines flight, departing Sat, Dec 19 from Chicago to Boston, returning Tue, Jan 12, priced at $220 Found 7 hours ago](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:BOS,departure:12/19/2026TANYT&leg2=from:BOS,to:MDW,departure:1/12/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:219.97&airProductToken=AQpgCi4IxnISBDE0NTgY7LABIMxwKJuhoAMwxaKgAzhSQABYAWoDRUNPcgdSMjFPWFA0Ci4IxnISBDMzNDgYzHAgwZMBKK2loAMw5qagAzhSQAFYAWoDRUNPcgdSMjFPWFA0CmAKLgjGchIEMTc3MxjBkwEg4FwoiqmiAzDNqqIDOFJAAFgBagNFQ09yB1IyMU9YUDQKLgjGchIEMjc3ORjgXCDssAEos6yiAzCvraIDOFJAAVgBagNFQ09yB1IyMU9YUDQSCggBEAEYASoCRjkYASIECAEQASgCKAMoBDAB)

Sat, Dec 19 - Tue, Jan 12 · MDW · BOS · Roundtrip

[Select Southwest Airlines flight, departing Thu, Dec 31 from Chicago to Boston, returning Tue, Jan 5, priced at $234 Just found](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:BOS,departure:12/31/2026TANYT&leg2=from:BOS,to:MDW,departure:1/5/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:233.38&airProductToken=AQoyCjAI15wBEgQyOTAyGOywASDBkwEo36ehAzDrqKEDOERAAFgBagNXR0FyB0RMTlZIMkYSCggBEAEYASoCV04YASIECAEQASgCKAMoBDAB)

Thu, Dec 31 - Tue, Jan 5 · MDW · BOS · Roundtrip

[Select American Airlines flight, departing Sat, Dec 19 from Chicago to Boston, returning Sat, Jan 9, priced at $239 Found 3 hours ago](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:BOS,departure:12/19/2026TANYT&leg2=from:BOS,to:ORD,departure:1/9/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:239.00&airProductToken=AQo0CjIIwYIBEgQ0NTcxGK4cIMGTASiPoaADMK-ioAM4QkAAWAFqBUJBU0lDcghPVkFKWlNCWBIKCAEQARgBKgJBQRgBIgQIARABKAIoAygEMAs)

Sat, Dec 19 - Sat, Jan 9 · ORD · BOS · Roundtrip

[Select American Airlines flight, departing Wed, Dec 23 from Chicago to Boston, returning Fri, Jan 1, priced at $247 Found 1 hour ago](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:BOS,departure:12/23/2026TANYT&leg2=from:BOS,to:ORD,departure:1/1/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:246.81&airProductToken=AQo0CjIIwYIBEgQ0Mzk4GK4cIMGTASiwx6ADMMvIoAM4QkAAWAFqBUJBU0lDcghPVkFKWlNCWAozCjEIwYIBEgM5NDcYwZMBIK4cKIusoQMwzK2hAzhCQABYAWoFQkFTSUNyCE9WQUpaU0JYEgoIARABGAEqAkFBGAEiBAgBEAEoAigDKAQwCw)

Wed, Dec 23 - Fri, Jan 1 · ORD · BOS · Roundtrip

[Select Southwest Airlines flight, departing Mon, Dec 21 from Chicago to Boston, returning Mon, Jan 4, priced at $247 Found 5 hours ago](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:BOS,departure:12/21/2026TANYT&leg2=from:BOS,to:MDW,departure:1/4/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:246.81&airProductToken=AQoyCjAI15wBEgQ0MTEzGOywASDBkwEo2bGgAzDgsqADOFZAAFgBagNXR0FyB1ZMTlZIMkYKMgowCNecARIEMjE4NRjBkwEg7LABKLXOoQMw2s-hAzhWQABYAWoDV0dBcgdWTE5WSDJGEgoIARABGAEqAldOGAEiBAgBEAEoAigDKAQwAQ)

Mon, Dec 21 - Mon, Jan 4 · MDW · BOS · Roundtrip

[Select United flight, departing Wed, Dec 23 from Chicago to Boston, returning Wed, Dec 30, priced at $247 Just found](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:BOS,departure:12/23/2026TANYT&leg2=from:BOS,to:ORD,departure:12/30/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:246.81&airProductToken=AQo5CjcI1YIBEgQxOTkwGK4cIMGTASjlzqADMPrPoAM4TkAAWAFqCjFfYmFzaWNlY29yCEtBQTJBSEJTCjkKNwjVggESBDE0MTQYwZMBIK4cKMWVoQMw%5F5ahAzhOQABYAWoKMV9iYXNpY2Vjb3IIS0FBMkFIQlMSCggBEAEYASoCVUEYASIECAEQASgCKAMoBDAL)

Wed, Dec 23 - Wed, Dec 30 · ORD · BOS · Roundtrip

[Select JetBlue Airways flight, departing Thu, Dec 17 from Chicago to Boston, returning Sun, Dec 20, priced at $257 Just found](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:BOS,departure:12/17/2026TANYT&leg2=from:BOS,to:ORD,departure:12/20/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:256.80&airProductToken=AQowCi4IwmwSBDEwMTIYrhwgwZMBKLOKoAMwxYugAzhMQABYAWoCRE5yCFBJMlFVRVkxEgoIARABGAEqAkI2GAEiBAgBEAEoAigDKAQwAQ)

Thu, Dec 17 - Sun, Dec 20 · ORD · BOS · Roundtrip

[Select Delta flight, departing Fri, Dec 25 from Chicago to Boston, returning Sat, Jan 2, priced at $282 Just found](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:BOS,departure:12/25/2026TANYT&leg2=from:BOS,to:ORD,departure:1/2/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:281.60&airProductToken=AQo4CjYIxJgBEgQ1Njg4GK4cIMGTASjt3qADMIbgoAM4RUAAWAFqCU1BSU5CQVNJQ3IIVkFWU0EwQkMKcQo3CMSYARIEMTAxORjBkwEg47QBKJa3oQMwpLihAzhFQABYAWoJTUFJTkJBU0lDcghWQVZTQTBCQwo2CMSYARIEMzg2OBjjtAEgrhwo8rihAzDVuaEDOEVAAVgBaglNQUlOQkFTSUNyCFZBVlNBMEJDEgoIARABGAEqAkRMGAEiBAgBEAEoAigDKAQwAQ)

Fri, Dec 25 - Sat, Jan 2 · ORD · BOS · Roundtrip

[Select Sun Country Airlines flight, departing Fri, Dec 25 from Chicago to Boston, returning Tue, Dec 29, priced at $516 Found 2 hours ago](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:BOS,departure:12/25/2026TANYT&leg2=from:BOS,to:ORD,departure:12/29/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:515.37&airProductToken=AQpVCigI07IBEgMyNjAYrhwgzHwotOCgAzCe4aADOFdAAFgBcgdXMlFBQ0FZCikI07IBEgMyNTMYzHwgwZMBKIvkoAMwsuWgAzhXQAFYAXIHVzJEQUNBWRIMCAEQARgBKgJTWTIAGAEiBAgBEAEoAigDKAQwAQ)

Fri, Dec 25 - Tue, Dec 29 · ORD · BOS · Roundtrip

[Select Alaska Airlines flight, departing Sat, May 29 from Chicago to Boston, returning Tue, Jun 1, priced at $593 Found 22 hours ago](https://www.expedia.com/Flights-Search?leg1=from:ORD,to:BOS,departure:5/29/2027TANYT&leg2=from:BOS,to:ORD,departure:6/1/2027TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&flp=mdl:flights-flex-module,price:592.40&airProductToken=AQphCi4IwaYBEgQxNDQ3GK4cIJJoKJKxrgMwm7OuAzhYQABYAWoCU1ZyCFFIME9BVkJOCi8IwaYBEgQxNTI2GJJoIMGTASiKta4DMOi3rgM4WEABWAFqAlNWcghHSDJPWFZCThIMCAEQARgBKgJBUzIAGAEiBAgBEAEoAigDKAQwAQ)

Sat, May 29 - Tue, Jun 1 · ORD · BOS · Roundtrip

## Alternative airports near Boston

Prices were available within the past 7 days. Prices and availability are subject to change.

[Select flight to Logan Intl. BOS. Cheapest and Closest option available. Average driving time to city center is 7 minutes. Flights from $455](https://www.expedia.com/Flights-Search?leg1=from:MDW,to:BOS,departure:11/28/2026TANYT&leg2=from:BOS,to:MDW,departure:12/3/2026TANYT&trip=roundtrip&passengers=adults:1,children:0,infantinlap:N&mode=search&pageId=0&sortOrder=INCREASING&sortType=PRICE)

7 min

## Find the cheapest month to fly from Chicago (CHI) to Boston (BOS)

### December is typically the cheapest month to fly

From $187 - $321 per traveler.

View flights in December

Insights are based on prices from searches for economy trips of 10 days or less on our sites in the last 12 months. Insights are informative only and current prices may differ.

## Book with confidence

### Chicago to Boston Flights

#### The cheapest times to fly from Chicago to Boston

On average, Thursday can be the cheapest time to fly, according to data from the Airlines Reporting Corporation (ARC), one of the world's biggest databases for global airline sales. The data reveals that you could save up to 16% by flying on a Thursday—the cheapest day to travel on average—instead of a Sunday—the most expensive. Some of the most affordable flights from Chicago to Boston are during the month of December. You can find some of the cheapest flights from Chicago to Boston with Expedia's search tool and vast selection of airlines.

#### The best time to book a flight from Chicago to Boston

Sunday is one of the best days to book for cheap flights from Chicago to Boston: Tickets reserved on a Sunday cost between 6% and 13% less than those reserved on a Friday, according to ARC data. The data also suggests booking early can also lead to cheaper airfares. You could save 24% by buying your tickets for domestic flights at least a month in advance and 10% by booking international flights 2 months in advance.

#### How to find cheap round-trip tickets from Chicago to Boston

Being flexible with your dates and using Expedia's Price Drop Protection and Price Tracking features are some of the best ways of finding a cheap ticket from Chicago to Boston in 2026\. You can also book with separate airlines for your outbound and return journeys, from $116 one-way. Expedia also offers Price Drop Protection, so if the cost of your airfare goes down after booking, you'll receive a credit for the difference\*. This is available for a small fee, and is free to One Key Gold and Platinum tier members.

Expedia's Price Tracking feature means you can stay on top of airfares without manually checking every day. It sends you automated price alerts for cheap Chicago to Boston flights and uses historical data to indicate when the best time to book is. Download Expedia's free app to activate this handy tool in a few easy taps.

You could also save big by booking one of Expedia's [vacation packages](https://www.expedia.com/package-deals). Bundling together your Chicago to Boston airfare with your accommodations and car rental is often cheaper than booking everything separately. There’s also One Key, Expedia's generous rewards program. Join for free and you could earn One Key cash on most bookings to save on future adventures.

*\*Terms apply.*

*Disclaimer: ARC The statistics are based on average round-trip ticket prices between January and August 2023\. The percentages you see are averages.*

## Travel information

| Origin airport      | Chicago, IL                 |
| ------------------- | --------------------------- |
| Destination airport | Logan International Airport |
| Distance            | 862 miles away              |
| Roundtrip price     | $220                        |

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- [Flights from Des Moines (DSM) to Boston (BOS)](https://www.expedia.com/lp/flights/dsm/bos/des-moines-to-boston)
- [Flights from Madison (MSN) to Boston (BOS)](https://www.expedia.com/lp/flights/msn/bos/madison-to-boston)
- [Flights from Santo Domingo (SDQ) to Boston (BOS)](https://www.expedia.com/lp/flights/sdq/bos/santo-domingo-to-boston)
- [Flights from Milwaukee (MKE) to Boston (BOS)](https://www.expedia.com/lp/flights/mke/bos/milwaukee-to-boston)
- [Flights from Tel Aviv (TLV) to Boston (BOS)](https://www.expedia.com/lp/flights/tlv/bos/tel-aviv-to-boston)
- [Flights from Barcelona (BCN) to Boston (BOS)](https://www.expedia.com/lp/flights/bcn/bos/barcelona-to-boston)
- [Flights from Salt Lake City (SLC) to Boston (BOS)](https://www.expedia.com/lp/flights/slc/bos/salt-lake-city-to-boston)
- [Flights from Birmingham (BHM) to Boston (BOS)](https://www.expedia.com/lp/flights/bhm/bos/birmingham-to-boston)
- [Flights from Newark Liberty Intl. Airport (EWR) to Boston (BOS)](https://www.expedia.com/lp/flights/ewr/bos/newark-liberty-intl-airport-to-boston)
- [Flights from Wilmington (ILM) to Boston (BOS)](https://www.expedia.com/lp/flights/ilm/bos/wilmington-to-boston)
- [Flights from Atlanta (ATL) to Boston (BOS)](https://www.expedia.com/lp/flights/atl/bos/atlanta-to-boston)
- [Flights from Orlando (MCO) to Boston (BOS)](https://www.expedia.com/lp/flights/mco/bos/orlando-to-boston)
- [Flights from St. Louis (STL) to Boston (BOS)](https://www.expedia.com/lp/flights/stl/bos/st-louis-to-boston)
- [Flights from Ontario Intl. Airport (ONT) to Boston (BOS)](https://www.expedia.com/lp/flights/ont/bos/ontario-to-boston)
- [Flights from Pittsburgh (PIT) to Boston (BOS)](https://www.expedia.com/lp/flights/pit/bos/pittsburgh-to-boston)
- [Flights from Rome (FCO) to Boston (BOS)](https://www.expedia.com/lp/flights/fco/bos/rome-to-boston)
- [Flights from Philadelphia (PHL) to Boston (BOS)](https://www.expedia.com/lp/flights/phl/bos/philadelphia-to-boston)
- [Flights from Austin (AUS) to Boston (BOS)](https://www.expedia.com/lp/flights/aus/bos/austin-to-boston)
- [Flights from Denver (DEN) to Boston (BOS)](https://www.expedia.com/lp/flights/den/bos/denver-to-boston)
- [Flights from Savannah (SAV) to Boston (BOS)](https://www.expedia.com/lp/flights/sav/bos/savannah-to-boston)
- [Flights from Knoxville (TYS) to Boston (BOS)](https://www.expedia.com/lp/flights/tys/bos/knoxville-to-boston)
- [Flights from Allentown (ABE) to Boston (BOS)](https://www.expedia.com/lp/flights/abe/bos/allentown-to-boston)
- [Flights from Shanghai (PVG) to Boston (BOS)](https://www.expedia.com/lp/flights/pvg/bos/shanghai-to-boston)
- [Flights from Memphis (MEM) to Boston (BOS)](https://www.expedia.com/lp/flights/mem/bos/memphis-to-boston)
- [Flights from Buffalo (BUF) to Boston (BOS)](https://www.expedia.com/lp/flights/buf/bos/buffalo-to-boston)
- [Flights from Houston (IAH) to Boston (BOS)](https://www.expedia.com/lp/flights/iah/bos/houston-to-boston)
- [Flights from Charleston (CHS) to Boston (BOS)](https://www.expedia.com/lp/flights/chs/bos/charleston-to-boston)
- [Flights from Tokyo (NRT) to Boston (BOS)](https://www.expedia.com/lp/flights/nrt/bos/tokyo-to-boston)
- [Flights from Greensboro (GSO) to Boston (BOS)](https://www.expedia.com/lp/flights/gso/bos/greensboro-to-boston)
- [Flights from Tucson (TUS) to Boston (BOS)](https://www.expedia.com/lp/flights/tus/bos/tucson-to-boston)
- [Flights from San Antonio (SAT) to Boston (BOS)](https://www.expedia.com/lp/flights/sat/bos/san-antonio-to-boston)
- [Flights from Fort Lauderdale (FLL) to Boston (BOS)](https://www.expedia.com/lp/flights/fll/bos/fort-lauderdale-to-boston)
- [Flights from Norfolk (ORF) to Boston (BOS)](https://www.expedia.com/lp/flights/orf/bos/norfolk-to-boston)
- [Flights from Bozeman (BZN) to Boston (BOS)](https://www.expedia.com/lp/flights/bzn/bos/bozeman-to-boston)
- [Flights from Cincinnati (CVG) to Boston (BOS)](https://www.expedia.com/lp/flights/cvg/bos/cincinnati-to-boston)
- [Flights from Madrid (MAD) to Boston (BOS)](https://www.expedia.com/lp/flights/mad/bos/madrid-to-boston)
- [Flights from Kansas City (MCI) to Boston (BOS)](https://www.expedia.com/lp/flights/mci/bos/kansas-city-to-boston)
- [Flights from Cleveland (CLE) to Boston (BOS)](https://www.expedia.com/lp/flights/cle/bos/cleveland-to-boston)
- [Flights from Little Rock (LIT) to Boston (BOS)](https://www.expedia.com/lp/flights/lit/bos/little-rock-to-boston)
- [Flights from Myrtle Beach (MYR) to Boston (BOS)](https://www.expedia.com/lp/flights/myr/bos/myrtle-beach-to-boston)
- [Flights from Toronto (YYZ) to Boston (BOS)](https://www.expedia.com/lp/flights/yyz/bos/toronto-to-boston)
- [Flights from Detroit (DTW) to Boston (BOS)](https://www.expedia.com/lp/flights/dtw/bos/detroit-to-boston)

\*Available to One Key members.

## Other language versions

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