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Cheap Flights from Chicago to Boston

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RatePunk searches hundreds of travel sites at once for deals on flights to Boston

Prices updated 24 days ago

486,190 searches this week

171 airlines compared

80%+ AI score for best value

Fares are subject to change and may not be available for all dates. (Data last updated May 29, 2026.)

Today’s best flight deals from Chicago to Boston

Explore current cheapest deals departing from Chicago to Boston

Round trip

Sort by: Cheapest

August 11 - August 18

Cheapest

ORD - Boston

$132

$123

Round trip

August 4 - August 11

Earliest

ORD - Boston

$130

$127

Round trip

August 18 - August 25

ORD - Boston

$133

$127

Round trip

September 8 - September 15

ORD - Boston

$157

$127

Round trip

September 10 - September 15

ORD - Boston

$161

$136

Round trip

August 26 - August 29

ORD - Boston

$230

$138

Round trip

August 15 - August 18

ORD - Boston

$231

$138

Round trip

August 20 - August 26

ORD - Boston

$134

$138

Round trip

August 5 - August 20

ORD - Boston

$110

$140

Round trip

September 2 - September 5

Best

ORD - Boston

$255

$140

Round trip

Unlock all 500+ flight deals to Boston and get alerts when great deals appear

Route Intelligence — 486,190 Searches this Week

Insights for flights from Chicago to Boston

Flights from Chicago to Boston typically range from $208–$524, with a median fare of $276. Right now, fares for cheap flights from Chicago to Boston are above the typical level. Only 4% of recent fares were classified as a good price, indicating that finding lower prices may require some flexibility. New deals appear almost daily, suggesting frequent opportunities to find better fares.

When is the cheapest time to fly from Chicago to Boston? The data indicates that December is typically the most affordable month, with a median fare of just $103. Following December, August offers median fares around $217, and September also presents competitive pricing with a median of $228. Planning your trip during these months could lead to significant savings.

For travelers flying from Chicago to Boston, 57.6% of recent fares are for direct flights. This means a meaningful share are non-stop, while the remaining itineraries typically involve 2 connections. Considering the prevalence of connecting flights, factoring in potential layover times is advisable when planning your journey.

How long is the flight from Chicago to Boston? A typical journey, including connections, takes approximately 5h 34m. This median duration accounts for both direct and connecting itineraries, providing a realistic expectation for your total travel time between the two cities. The overall distance between Chicago and Boston is 1391 km, classifying it as a short-haul route.

How much is a round trip from Chicago to Boston

Regular price: $100 - $224

Prices for flights from Chicago to Boston are currently within the regular range.

The regular price range for this route is $100 to $224. The current lowest deal is $123 with JetBlue Airways, for travel from August 11 to August 18.

now $123

Low $100

High $224

The cheapest time to fly from Chicago to Boston

The cheapest month to fly from Chicago to Boston is December, with a median price of $103. The most expensive month is March, with a median price of $569. Prices are generally lower from January to December.

December

Cheapest

Flights from $103

March

Most Expensive

Flights from $569

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Direct flights from Chicago to Boston

JetBlue Airways

Last-minute flights going from Chicago to Boston

Thu, Jul 2

⌛ Last-Minute

ORD - Boston

Chicago (ORD) - Boston (BOS)

JetBlue Airways

$282

$164

One-way

Thu, Jul 2

⌛ Last-Minute

ORD - Boston

Chicago (ORD) - Boston (BOS)

JetBlue Airways

$267

$170

One-way

Fri, Jul 3

⌛ Last-Minute

ORD - Boston

Chicago (ORD) - Boston (BOS)

JetBlue Airways

$275

$167

One-way

Fri, Jul 3

⌛ Last-Minute

ORD - Boston

Chicago (ORD) - Boston (BOS)

JetBlue Airways

$273

$171

One-way

Sat, Jul 4

⌛ Last-Minute

MDW - Boston

Chicago (MDW) - Boston (BOS)

Southwest Airlines

$205

$149

One-way

Tue, Jul 7

⌛ Last-Minute

ORD - Boston

Chicago (ORD) - Boston (BOS)

United Airlines

$154

$149

One-way

Biggest price drops on these dates for flights from Chicago to Boston

3 nights

Oct 17 - Oct 20

$341 → $182

47%

7 nights

Oct 24 - Oct 31

$331 → $180

46%

4 nights

Oct 22 - Oct 26

$341 → $191

44%

4 nights

Oct 15 - Oct 19

$341 → $195

43%

Popular Airports to fly from Chicago to Boston

Chicago - Boston route insights

💸 Price insights

Recent fares are above the typical level

Recent fares for Chicago to Boston are above the typical level, with a median price of $276.

📅 Best time to fly

Fly in December for the best prices

Historically, December offers the lowest median price at $103, making it the cheapest month to fly.

⏱️ Flight duration

Median flight time is 5h 34m

The median flight time from Chicago to Boston is 5 hours and 34 minutes.

✈️ Airlines & availability

Direct flights are frequent

Direct flights are frequent, accounting for 57.6% of deals, with JetBlue Airways offering direct routes.

🏆 Airline highlight

JetBlue Airways offers direct flights

JetBlue Airways is a key airline for direct flights on the Chicago to Boston route.

🎯 Booking tip

Deals appear frequently

Deals for flights from Chicago to Boston appear frequently, with over 1 deal per day.

Chicago main airports to depart from

O Hare International (ORD)

Cheapest

Depart from O'Hare International for flights to Boston, often offering competitive prices.

📍 ~25 km from Chicago city center (reachable by car or train)

💸 Flights from ~$123

Chicago Midway International (MDW)

Consider Chicago Midway International for your flight to Boston.

📍 ~15 km from Chicago city center (reachable by car or train)

💸 Flights from ~$141

Chicago Rockford International (RFD)

Chicago Rockford International is an option for flights from the wider Chicago area to Boston.

📍 ~120 km from Chicago city center (reachable by car)

💸 Flights from ~$253

Boston main airports to arrive at

Logan International (BOS)

Cheapest

Logan International Airport is a convenient arrival point for flights from Chicago to Boston.

📍 ~5 km from city center (reachable by car, public transport)

💸 Flights from ~$123

Airports nearby Boston used as alternative

Rhode Island T. F. Green Int'l Airport (PVD)

This airport is a major regional alternative with a wide range of domestic and some international connections.

📍 ~60 km from Boston (reachable by car or commuter rail)

💸 Flights from ~$273

Manchester–Boston Regional (MHT)

This airport is a primary alternative for travelers north of Boston, offering a strong domestic network.

📍 ~80 km from Boston (reachable by car)

💸 Flights from ~$270

Bradley International (BDL)

This large international airport serves as a major hub for Southern New England with diverse destination options.

📍 ~140 km from Boston (reachable by car)

💸 Flights from ~$195

Portland International Jetport (PWM)

Cheapest

This highly reliable regional jetport offers good connectivity for travelers heading to Maine or northern suburbs.

📍 ~160 km from Boston (reachable by car)

💸 Flights from ~$169

Worcester Regional (ORH)

This airport is geographically close to the western Boston suburbs, offering a low-stress environment.

📍 ~70 km from Boston (reachable by car)

💸 Flights from ~$192

Business & First Class Flight Deals to Boston

Boston, United States

38% AI deal score

$12,970

From ORD

Elite

Sep 14

Boston, United States

38% AI deal score

$12,970

Frequently Asked Questions About Flights to Boston

Historically, the optimal booking window for flights from Chicago to Boston is typically 14-27 days before departure. Flights booked within this period have an average price of $287. Booking 7-13 days out sees an average price of $334, while waiting until 0-6 days before departure typically results in a higher average price of $379. For those planning further ahead, flights booked 28-59 days in advance average $464.

Across the trailing quarter, a good price for a flight from Chicago to Boston is considered to be $208 or less. The median price for this route was $276, with 25% of fares falling at or below $208. Conversely, 75% of fares were $524 or less, indicating that prices can vary significantly.

Historically, December has been the cheapest month to fly from Chicago to Boston, with a median price of $103. August and September also offer relatively lower median prices, at $217 and $228 respectively. The annual median price for this route is $276, suggesting that these months provide opportunities for savings compared to the yearly average.

Related routes

Consider alternative routes from Chicago

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Cheap Flights from Chicago to Boston

Today’s best flight deals from Chicago to Boston

Unlock all 500+ flight deals to Boston and get alerts when great deals appear

Route Intelligence — 486,190 Searches this Week

Insights for flights from Chicago to Boston

How much is a round trip from Chicago to Boston

The cheapest time to fly from Chicago to Boston

Direct flights from Chicago to Boston

Last-minute flights going from Chicago to Boston

Biggest price drops on these dates for flights from Chicago to Boston

Popular Airports to fly from Chicago to Boston

Chicago - Boston route insights

Recent fares are above the typical level

Fly in December for the best prices

Median flight time is 5h 34m

Direct flights are frequent

JetBlue Airways offers direct flights

Deals appear frequently

Chicago main airports to depart from

Boston main airports to arrive at

Airports nearby Boston used as alternative

Business & First Class Flight Deals to Boston

Best Elite deals to Boston

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Frequently Asked Questions About Flights to Boston

How far in advance should I book a flight from Chicago to Boston?