Flights from Chicago to Boston from $50

This is the cheapest one-way flight price, found on 8/16. Prices may vary by date and flight preferences.

CHI — BOS

Aug 23 — Aug 301

Round-tripOne-wayMulti-city

Wed 8/23

Wed 8/30

1 adult

Economy

The best prices from Chicago to Boston Logan Intl are usually found in February or January, booked 13 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

How to find the cheapest flight from Chicago (CHI) to Boston (BOS)

Tips, tricks and FAQs for finding the best Chicago to Boston flight prices.

Popular in	June
Cheapest in	February
Round-trip from	$198
One-way from	$70

High demand for flights, 25% potential price rise

Search Deals

Best time to find cheap flights, 33% potential price drop

Search Deals

From Chicago (CHI) to Boston Logan Intl

Search Deals

One-way flight from Chicago (CHI) to Boston Logan Intl

Search Deals

CHI - BOS Price	$198 - $403
BOS Temperature	30.2 - 73.4 °F
BOS Rainfall	3.1 - 4 inches

CHI - BOS

Price

$198 - $403

BOS

Temperature

30.2 - 73.4 °F

BOS

Rainfall

3.1 - 4 inches

Monday is generally the cheapest day of the week to fly from Chicago to Boston. Saturday is the most expensive.

With prices from $118, February is the best time of year for Chicago - Boston flights. Although prices in February can rise to about $236, this still represents a 32% reduction from June, the most expensive time of the year for Boston flights.

Flying from Chicago to Boston in the evening is the cheapest time of day to take this flight route. If your travel plans are flexible enough to fly during this part of the day, then you can expect to save around 19% on your trip compared to booking a flight at noon (which tends to be more expensive).

August and September flight deals from Chicago to Boston

The best CHI - BOS flight prices departing in the next 6 weeks.

These are some of the best deals we've found on flights to Boston in 2023 at this time. If these deals don't appeal to you, be sure to come back soon for more options.

Tue 9/199:19 amORD - BOS

1 stop18h 33mFrontier

Sat 9/235:42 amBOS - ORD

1 stop8h 56mFrontier

Deal found 8/16$102

Sat 9/162:47 pmMDW - BOS

1 stop12h 55mFrontier

Tue 9/195:52 amBOS - MDW

1 stop24h 33mFrontier

Deal found 8/17$102

Fri 9/811:35 amORD - BOS

1 stop6h 05mMultiple Airlines

Mon 9/115:27 amBOS - ORD

1 stop9h 16mMultiple Airlines

Deal found 8/16$104

Thu 9/281:00 amORD - BOS

1 stop13h 31mMultiple Airlines

Sat 10/145:30 amBOS - ORD

1 stop9h 14mMultiple Airlines

Deal found 8/17$106

Sat 9/92:47 pmMDW - BOS

1 stop12h 55mFrontier

Wed 9/138:59 amBOS - MDW

1 stop5h 25mFrontier

Deal found 8/17$108

Sat 9/302:48 pmORD - BOS

1 stop12h 54mMultiple Airlines

Wed 10/1812:00 pmBOS - ORD

1 stop8h 54mMultiple Airlines

Deal found 8/17$109

Wed 9/136:50 amORD - BOS

1 stop7h 11mSpirit Airlines

Wed 9/201:30 pmBOS - ORD

1 stop7h 38mSpirit Airlines

Deal found 8/16$110

Mon 9/1111:35 amORD - BOS

1 stop7h 10mSpirit Airlines

Tue 9/197:19 amBOS - ORD

1 stop11h 46mSpirit Airlines

Deal found 8/17$111

Sun 9/171:24 pmORD - BOS

1 stop14h 13mFrontier

Tue 9/195:52 amBOS - ORD

1 stop28h 16mFrontier

Deal found 8/17$112

Cheap flights from Chicago to Boston in 2023

The best Chicago - Boston flight prices departing in 2023.

These are some of the best deals we've found on flights to Boston in 2023 at this time. If these deals don't appeal to you, be sure to come back soon for more options.

Tue 9/199:19 amORD - BOS

1 stop18h 33mFrontier

Sat 9/235:42 amBOS - ORD

1 stop8h 56mFrontier

Deal found 8/16$102

Sat 9/162:47 pmMDW - BOS

1 stop12h 55mFrontier

Tue 9/195:52 amBOS - MDW

1 stop24h 33mFrontier

Deal found 8/17$102

Fri 9/811:35 amORD - BOS

1 stop6h 05mMultiple Airlines

Mon 9/115:27 amBOS - ORD

1 stop9h 16mMultiple Airlines

Deal found 8/16$104

Thu 9/281:00 amORD - BOS

1 stop13h 31mMultiple Airlines

Sat 10/145:30 amBOS - ORD

1 stop9h 14mMultiple Airlines

Deal found 8/17$106

Thu 10/121:17 pmMDW - BOS

1 stop14h 13mFrontier

Tue 10/177:49 amBOS - MDW

1 stop7h 35mFrontier

Deal found 8/17$108

Mon 10/22:38 pmORD - BOS

1 stop13h 14mMultiple Airlines

Wed 10/1810:48 amBOS - ORD

1 stop10h 06mMultiple Airlines

Deal found 8/17$109

Sat 10/216:45 amORD - BOS

1 stop9h 05mSpirit Airlines

Wed 10/2510:48 amBOS - ORD

1 stop10h 06mSpirit Airlines

Deal found 8/17$110

Mon 9/1111:35 amORD - BOS

1 stop7h 10mSpirit Airlines

Tue 9/197:19 amBOS - ORD

1 stop11h 46mSpirit Airlines

Deal found 8/17$111

Sun 9/171:24 pmORD - BOS

1 stop14h 13mFrontier

Tue 9/195:52 amBOS - ORD

1 stop28h 16mFrontier

Deal found 8/17$112

Cheap Frontier flights from Chicago to Boston

Take a peek at the cheapest Frontier flights we've detected traveling from Chicago to Boston. Make sure to double check the flight details before booking.

Tue 9/199:19 amORD - BOS

1 stop18h 33mFrontier

Sat 9/235:42 amBOS - ORD

1 stop8h 56mFrontier

Deal found 8/16$102

Thu 10/121:17 pmMDW - BOS

1 stop14h 13mFrontier

Tue 10/177:49 amBOS - MDW

1 stop7h 35mFrontier

Deal found 8/17$108

Fri 9/158:27 amMDW - BOS

1 stop19h 15mFrontier

Sat 9/238:59 amBOS - MDW

1 stop6h 25mFrontier

Deal found 8/16$112

Sun 9/1012:48 pmMDW - BOS

1 stop14h 49mFrontier

Wed 9/138:59 amBOS - MDW

1 stop5h 25mFrontier

Deal found 8/17$118

Sun 10/112:48 pmMDW - BOS

1 stop14h 49mFrontier

Tue 10/177:49 amBOS - MDW

1 stop7h 35mFrontier

Deal found 8/17$119

Fri 9/88:27 amMDW - BOS

1 stop19h 15mFrontier

Sun 9/105:36 amBOS - MDW

1 stop7h 22mFrontier

Deal found 8/17$123

Sun 9/1712:48 pmMDW - BOS

1 stop14h 49mFrontier

Sun 9/245:36 amBOS - MDW

1 stop7h 22mFrontier

Deal found 8/17$128

Sun 10/112:48 pmMDW - BOS

1 stop14h 49mFrontier

Fri 10/135:30 amBOS - MDW

1 stop7h 57mFrontier

Deal found 8/17$129

Wed 8/2311:53 amORD - BOS

1 stop15h 47mFrontier

Sun 8/275:40 amBOS - ORD

1 stop7h 57mFrontier

Deal found 8/17$268

One of the most popular airlines traveling from Chicago to Boston is Frontier. Flights on this route from Frontier typically cost $228.60 RT, a price that is 45% more expensive than the average Chicago to Boston flight. The cheapest flight found was $79 RT. When traveling from Chicago to Boston on Frontier, the most popular airport to depart from is Chicago O'Hare Intl Airport and the most popular airport to arrive at is Boston Logan Intl Airport. When flying from Chicago to Boston, Frontier flights are -100% more popular than any other airline flying that same route.

Cheap Spirit Airlines flights from Chicago to Boston

Take a gander at the lowest prices we've found on Spirit Airlines flights from Chicago to Boston. Deals frequently update to provide users with more options.

Wed 9/136:50 amORD - BOS

1 stop7h 11mSpirit Airlines

Wed 9/201:30 pmBOS - ORD

1 stop7h 38mSpirit Airlines

Deal found 8/16$110

Mon 9/1111:35 amORD - BOS

1 stop7h 10mSpirit Airlines

Tue 9/197:19 amBOS - ORD

1 stop11h 46mSpirit Airlines

Deal found 8/17$111

Tue 9/125:33 amORD - BOS

1 stop13h 12mSpirit Airlines

Tue 9/197:19 amBOS - ORD

2 stops22h 24mSpirit Airlines

Deal found 8/17$113

Fri 9/811:35 amORD - BOS

1 stop6h 05mSpirit Airlines

Thu 9/142:00 amBOS - ORD

1 stop10h 21mSpirit Airlines

Deal found 8/17$115

Thu 9/75:33 amORD - BOS

1 stop13h 56mSpirit Airlines

Mon 9/114:59 pmBOS - ORD

2 stops17h 15mSpirit Airlines

Deal found 8/16$116

Thu 10/1211:39 amORD - BOS

1 stop8h 08mSpirit Airlines

Tue 10/172:00 amBOS - ORD

1 stop13h 13mSpirit Airlines

Deal found 8/17$117

Wed 8/3012:20 pmORD - BOS

2 stops18h 07mSpirit Airlines

Fri 9/225:55 pmBOS - ORD

1 stop12h 54mSpirit Airlines

Deal found 8/16$118

Fri 9/811:35 amORD - BOS

1 stop6h 05mSpirit Airlines

Mon 9/115:55 pmBOS - ORD

2 stops16h 19mSpirit Airlines

Deal found 8/16$119

Thu 10/1211:39 amORD - BOS

1 stop8h 08mSpirit Airlines

Tue 10/177:18 amBOS - ORD

1 stop11h 47mSpirit Airlines

Deal found 8/17$121

Spirit Airlines is one of the most popular airlines used for those traveling from Chicago to Boston. Flights on this route from Spirit Airlines typically cost $326.03 RT, a price that is 34% more expensive than the average Chicago to Boston flight. The cheapest flight found was $79 RT. When traveling from Chicago to Boston on Spirit Airlines, the most popular airport to depart from is Chicago O'Hare Intl Airport and the most popular airport to arrive at is Boston Logan Intl Airport. When flying from Chicago to Boston, Spirit Airlines flights are -100% more popular than any other airline flying that same route.

Non-stop flights to Boston from Chicago

Save time with Chicago to Boston direct flight deals

For a quicker trip, book one of these direct flights from Chicago to Boston. Users seeking other options on flights from Chicago to Boston should update the search form at the top of the page.

Thu 9/74:30 pmORD - BOS

Nonstop2h 24mJetBlue

Sat 9/91:35 pmBOS - ORD

Nonstop2h 59mJetBlue

Deal found 8/17$153

Tue 10/316:30 amORD - BOS

Nonstop2h 25mDelta

Sat 11/410:17 amBOS - ORD

Nonstop2h 48mDelta

Deal found 8/17$156

Fri 9/155:30 pmORD - BOS

Nonstop2h 27mUnited Airlines

Tue 9/198:46 amBOS - ORD

Nonstop2h 51mUnited Airlines

Deal found 8/17$158

Wed 8/302:00 amORD - BOS

Nonstop2h 22mUnited Airlines

Wed 9/61:08 pmBOS - ORD

Nonstop2h 47mUnited Airlines

Deal found 8/17$163

Wed 8/302:00 amORD - BOS

Nonstop2h 22mUnited Airlines

Mon 9/42:00 amBOS - ORD

Nonstop2h 47mUnited Airlines

Deal found 8/17$168

Tue 10/316:30 amORD - BOS

Nonstop2h 25mDelta

Fri 11/32:15 amBOS - ORD

Nonstop2h 49mDelta

Deal found 8/17$170

Thu 9/74:22 pmORD - BOS

Nonstop2h 22mAmerican Airlines

Sun 9/101:35 amBOS - ORD

Nonstop2h 54mAmerican Airlines

Deal found 8/17$173

Wed 8/302:00 amORD - BOS

Nonstop2h 22mUnited Airlines

Sun 9/33:38 amBOS - ORD

Nonstop2h 49mUnited Airlines

Deal found 8/17$178

Wed 8/308:33 amORD - BOS

Nonstop2h 32mJetBlue

Wed 9/61:35 pmBOS - ORD

Nonstop2h 59mJetBlue

Deal found 8/17$183

Last minute flights from Chicago to Boston

Late deals on return flights to Boston from Chicago, departing today and this week

Have a look at some of the flights available from Chicago to Boston departing last-minute. It's wise to confirm all flight details are correct before booking.

Wed 8/232:00 amORD - BOS

Nonstop2h 22mUnited Airlines

Wed 8/303:38 amBOS - ORD

Nonstop2h 49mUnited Airlines

Deal found 8/16$168

Wed 8/232:00 amORD - BOS

Nonstop2h 22mUnited Airlines

Wed 8/301:45 amBOS - ORD

1 stop4h 39mUnited Airlines

Deal found 8/16$178

Wed 8/2311:53 amORD - BOS

1 stop15h 47mMultiple Airlines

Wed 8/308:51 amBOS - ORD

1 stop9h 37mMultiple Airlines

Deal found 8/16$187

Thu 8/242:00 amORD - BOS

Nonstop2h 15mDelta

Sat 8/261:30 pmBOS - ORD

Nonstop3h 04mDelta

Deal found 8/17$188

Wed 8/2311:53 amORD - BOS

1 stop15h 47mMultiple Airlines

Thu 8/317:25 amBOS - ORD

1 stop8h 33mMultiple Airlines

Deal found 8/17$190

Sat 8/265:50 amORD - BOS

1 stop4h 41mAmerican Airlines

Mon 8/281:47 amBOS - ORD

Nonstop2h 53mAmerican Airlines

Deal found 8/17$198

Fri 8/2512:19 pmORD - BOS

1 stop3h 49mAmerican Airlines

Mon 8/281:47 amBOS - ORD

Nonstop2h 53mAmerican Airlines

Deal found 8/17$202

Sat 8/265:50 amORD - BOS

1 stop4h 41mAmerican Airlines

Tue 8/294:00 amBOS - ORD

1 stop5h 21mAmerican Airlines

Deal found 8/17$205

Wed 8/2311:53 amORD - BOS

1 stop15h 47mMultiple Airlines

Fri 8/253:55 pmBOS - ORD

1 stop17h 26mMultiple Airlines

Deal found 8/16$206

One-way flights from Chicago to Boston

The best deals found for one-way Chicago - Boston flights.

Users in need of a one-way flight from Chicago to Boston can choose from these deals. Users needing a return flight from Chicago to Boston should utilize the search form above.

Wed 9/271:00 amORD - BOS

1 stop13h 01mSpirit Airlines

Deal found 8/16$50

Sat 9/95:33 amORD - BOS

1 stop12h 07mSpirit Airlines

Deal found 8/17$55

Thu 9/76:50 amORD - BOS

1 stop7h 41mSpirit Airlines

Deal found 8/17$56

Sat 9/166:50 amORD - BOS

1 stop12h 09mSpirit Airlines

Deal found 8/16$57

Thu 9/146:05 amMDW - BOS

1 stop21h 37mFrontier

Deal found 8/17$57

Sat 9/162:47 pmMDW - BOS

1 stop12h 55mFrontier

Deal found 8/17$58

Wed 9/203:00 amORD - BOS

2 stops11h 15mSpirit Airlines

Deal found 8/17$59

Tue 10/171:17 pmMDW - BOS

1 stop14h 13mFrontier

Deal found 8/17$60

Fri 9/2212:54 pmORD - BOS

1 stop7h 13mSpirit Airlines

Deal found 8/17$61

Find flights from Chicago to Boston within your budget

Use the slider to find flights from Chicago to Boston that fit your budget.

Fly from

Fly to

Budget

$102 - $209

Route

Depart

Return

Price

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 9/19

1 stop18h 33m

Boston Logan Intl

Sat 9/23

1 stop8h 56m

$102

Pick Dates

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

Sat 9/16

1 stop12h 55m

Boston Logan Intl

Tue 9/19

1 stop24h 33m

$102

Pick Dates

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 9/7

1 stop13h 56m

Boston Logan Intl

Sat 9/9

1 stop8h 56m

$104

Pick Dates

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/13

1 stop7h 11m

Boston Logan Intl

Wed 9/20

1 stop7h 38m

$110

Pick Dates

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 9/7

Nonstop2h 24m

Boston Logan Intl

Sat 9/9

Nonstop2h 59m

$153

Pick Dates

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 9/15

Nonstop2h 27m

Boston Logan Intl

Tue 9/19

Nonstop2h 51m

$158

Pick Dates

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 9/8

1 stop4h 37m

Boston Logan Intl

Thu 9/14

Nonstop2h 54m

$186

Pick Dates

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Thu 10/19

Nonstop2h 23m

Boston Logan Intl

Tue 10/24

Nonstop2h 46m

$198

Pick Dates

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

Sun 8/27

Nonstop2h 10m

Boston Logan Intl

Wed 8/30

Nonstop2h 35m

$209

Pick Dates

Flights are sorted by cheapest first

Deals found on 8/16

Related info for your journey

See answers for the most popular questions asked about this flight route.

Boston Logan Intl is the name of the Boston airport you fly into if you book a flight from Chicago. The BOS airport handles roughly 57 inbound flights originating from Chicago per day. For this route, 7 airlines have flights from Chicago to Logan Intl. If you plan on staying somewhere in the center of Boston, it’s 2.6 mi from Boston Logan Intl.

On Priceline, users have found cheap flights from Chicago to Boston for as low as $200. The average price found was around $113, however the best flight deal found in the last week was $102 (a Frontier flight from Chicago to Boston).

Yes. Over 20 direct flights from Chicago to Boston were found in the last week, with better deals found between $200 and $183.

$200 is the best price for last minute Chicago to Boston flights. Priceline has found over 20 Chicago - Boston flights departing in the next week.

You can find a nonstop flight on these days: Sunday, Monday, Tuesday, Wednesday, Friday, Saturday.

Those looking to book a flight to Boston from Chicago can expect to see 20 flights per day on average.
Morning (6am - Noon) - 25% of flight departures
Afternoon (Noon - 6pm) - 30% of flight departures
Evening (6pm - Midnight) - 45% of flight departures

7h 11m is the fastest flight time between Boston and Chicago. Frontier and Spirit Airlines provide the fastest flights for this route. You can anticipate the flight duration to vary by 11h 22m on average. At the moment, Frontier offers the quickest flight for as low as $102 per ticket. Roughly 869 mi separate Chicago from Boston. Flight options will be for both nonstop flights and flights with stops.

Priceline users recently found round-trip flights from Chicago to Boston starting at $102 per ticket. Another airline offering cheap airfare from Chicago to Boston is Spirit Airlines. Frontier has flights to Boston for 56% less than the average price available within the next 90 days.

Spirit Airlines is the cheapest airline flying one-way from Chicago to Boston. Priceline users have recently found flights for as cheap as $50. Keep your eyes open for deals from either Frontier or JetBlue. These two airlines can also get you from Chicago to Boston for a low one-way price.

Undisclosed Carrier, American Airlines and Alaska Airlines are the most popular airlines when flying from Chicago to Boston.

Envoy Air, Azul, and United Airlines arrive at Boston on schedule the most often. They avoid delays on between 74% to 89% flights from Chicago to Boston.

Finding a cheap flight from Chicago to Boston means finding a price under $380. The best price found recently was $84. The most popular route, Chicago O'Hare Intl - Boston Logan Intl, averages around $104.

The travel industry and airlines use IATA (International Air Transport Association) codes like ORD to BOS for calling airports. A flight from ORD to BOS would be a different way of saying a flight from Chicago O'Hare Intl Airport to Boston Logan Intl Airport, essentially. Here are other airport codes related to this flight route that might be useful: Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD).

More flights from Chicago

Midway to Knoxville

Midway to Atlanta

O'Hare Intl to Atlanta

Midway to Raleigh

Midway to Asheville

Midway to Denver

More flights to Boston

Miami to Boston

Myrtle Beach to Boston

Charlotte to Boston

Orlando to Boston

Fort Lauderdale to Boston

Philadelphia to Boston

More flights to Boston from Chicago

Flights to Chicago

Flights to Boston

Find a rental car for your trip

Car Rentals in Boston

Airlines that fly from Chicago to Boston

See the airlines flying to Boston from Chicago over the last 12 months, their prices and their punctuality.

Airline	Cheapest	Average	Flexibility	On-time
JetBlue	Cheapest$79	Average$229	FlexibilityNo cancel fee	On-time62%	Search JetBlue flights
Delta	Cheapest$79	Average$326	FlexibilityNo cancel fee	On-timeN/A	Search Delta flights
United Airlines	Cheapest$89	Average$281	FlexibilityNo cancel fee	On-time69%	Search United Airlines flights
American Airlines	Cheapest$109	Average$255	FlexibilityNo cancel fee	On-time71%	Search American Airlines flights
Spirit Airlines	Cheapest$119	Average$191	FlexibilityNo cancel fee	On-time65%	Search Spirit Airlines flights
Alaska Airlines	Cheapest$228	Average$356	FlexibilityNo cancel fee	On-time75%	Search Alaska Airlines flights

What time of day do Chicago to Boston flights depart?

A summary of when current Chicago - Boston flight route schedules depart.

12%of flight departures	Early morningMidnight to 6 am
42%of flight departures	Morning6 am to noon
24%of flight departures	AfternoonNoon to 6 pm
22%of flight departures	Evening6 pm to midnight

Midnight

6 AM

Noon

6 PM

What days of the week do Chicago to Boston flights depart?

A summary of the days of the week where flights depart Chicago for Boston.

Sunday	60daily flights
Monday	65daily flights
Tuesday	57daily flights
Wednesday	57daily flights
Thursday	60daily flights
Friday	58daily flights
Saturday	44daily flights

Flights from Chicago to Boston from $50 | Priceline (2024)

FAQs

How does Priceline get cheap flights? ›

Priceline is an OTA that works as a middleman between customers and the airlines. It displays all the available flights offered by the airlines and when you book a flight via Priceline, it then purchases that flight from the airline and sells it to you, the customer.

How does booking a flight on Priceline work? ›

To book a Priceline flight:

Go to www.priceline.com and click Flights.
Enter criteria to search for suitable flights.
Select from available flights.
Enter insurance preference and each traveler's information.
Select seats for each passenger on each flight.
Enter your billing information and confirm your order.

Mar 17, 2022

View Details ›

Does Priceline do airlines? ›

Priceline is an online travel agency (OTA) you can use to book flights, hotels, rental cars and more.

Learn More ›

What airlines does Priceline use? ›

The benefit of searching for travel through Priceline is that it will bring back search results from a number of different companies. This means that if you search for a flight, you'll get information about United Airlines, Delta Air Lines, Alaska Airlines and American Airlines all at once.

What day is Priceline cheapest? ›

“Priceline analysts found that the best day of week to book a hotel for the lowest prices was on Sunday,” Nagle said. “The second-best day of week to book a hotel was Monday, and the difference was not large.”

Show Me More ›

Is Priceline or Expedia better? ›

Still, Priceline.com routinely offers better pricing. In comparing Expedia vs. Priceline, you will also find that Priceline has much higher-rated customer service. If you don't already have a profile with either program, we recommend that you start with Priceline because its customer service has a better reputation.

Do you have to pay upfront with Priceline? ›

When booking a hotel through Priceline, you may have the option to choose between prepaid and pay at the hotel options. Prepaid reservations require you to pay for the room in full at the time of booking.

Get More Info ›

Does Priceline charge a fee? ›

Priceline Processing Fees: A non-refundable per ticket processing fee may apply to airline reservations. The fee amount varies and will be displayed on your Contract page.

Discover More Details ›

Why is hot wire so cheap? ›

By hiding hotel names, Hotwire and Priceline are able to offer lower prices until rooms are sold because only the purchasers will know exactly how low the price has temporarily fallen.

Show Me More ›

How far out should you book a flight? ›

Best Time To Book Domestic Flights

The Expedia study found that the sweet spot is 28 to 35 days before departure while the Google study found prices bottomed out 44 days before departure. However, both studies agree that you don't want to wait until the last minute. Book at least 21 days before departure.

Show Me More ›

What airline is not on Priceline? ›

Southwest has long prevented third-party sites and apps from selling its fares, which is why you'll never see Southwest on Google Flights or Priceline.

Learn More Now ›

Does Southwest Airlines use Priceline? ›

“Unlike most other airlines, Southwest does not use online travel agencies to market or sell tickets. ”

Show Me More ›

What is pay later on Priceline? ›

Priceline payment plans with Affirm: book now pay later with no fees. Take a trip now without paying for it all at once. Book your next flight, hotel, rental car, or vacation package at Priceline and pay over time with Affirm.

What is the new name for Priceline? ›

Priceline Group renamed itself to Booking Holdings Inc. on Wednesday to better reflect its growing portfolio of brands and highlight booking.com, the underlying driver of its business, according to CEO Glenn Fogel.

What's an express deal on Priceline? ›

Express Deals match you to an exclusive collection of rental car companies, hotel properties, or flight carriers offering the biggest discounts. In exchange for these low prices, we reveal the company/property/carrier's name only after you book.

Get More Info ›

How much commission does Priceline take? ›

Terms of the Affiliate Program

The Priceline affiliate commission rate varies between 3 and 5%. For flights, you will receive the lowest commission.

See Details ›

What is the pricing strategy of Priceline com? ›

Priceline is best known for its name-your-own-price format, in which consumers bid for services but not for ser- vice providers. Because Priceline serves as an opaque selling mechanism, it attracts price-conscious consumers.

Learn More ›

Are Priceline prices guaranteed? ›

Priceline's Best Price Guarantee (BPG) policy gives its VIP members the ability to book with confidence and is one of the many benefits of the VIP program. If a VIP member finds a better price within 24 hours of booking on a reservation that qualifies under our BPG policy, we'll refund the difference.

How does Priceline make money? ›

Priceline solves this problem by quietly selling off supply overhang while simultaneously giving the consumer an illusion of a hard fought exclusive deal. Meanwhile they take the difference between what the consumer is willing to pay and the supplier is willing to sell to turn a tidy profit.

Show Me More ›

Flights from Chicago to Boston from $50 | Priceline (2024)

This is the cheapest one-way flight price, found on 8/16. Prices may vary by date and flight preferences.

The best prices from Chicago to Boston Logan Intl are usually found in February or January, booked 13 days in advance, depart on a Tuesday or Wednesday and return on a Tuesday

How to find the cheapest flight from Chicago (CHI) to Boston (BOS)

Tips, tricks and FAQs for finding the best Chicago to Boston flight prices.

Popular in

Cheapest in

Round-trip from

One-way from

August and September flight deals from Chicago to Boston

The best CHI - BOS flight prices departing in the next 6 weeks.

These are some of the best deals we've found on flights to Boston in 2023 at this time. If these deals don't appeal to you, be sure to come back soon for more options.

Cheap flights from Chicago to Boston in 2023

The best Chicago - Boston flight prices departing in 2023.

These are some of the best deals we've found on flights to Boston in 2023 at this time. If these deals don't appeal to you, be sure to come back soon for more options.

Cheap Frontier flights from Chicago to Boston

Take a peek at the cheapest Frontier flights we've detected traveling from Chicago to Boston. Make sure to double check the flight details before booking.

Cheap Spirit Airlines flights from Chicago to Boston

Take a gander at the lowest prices we've found on Spirit Airlines flights from Chicago to Boston. Deals frequently update to provide users with more options.

Non-stop flights to Boston from Chicago

Save time with Chicago to Boston direct flight deals

For a quicker trip, book one of these direct flights from Chicago to Boston. Users seeking other options on flights from Chicago to Boston should update the search form at the top of the page.

Last minute flights from Chicago to Boston

Late deals on return flights to Boston from Chicago, departing today and this week

Have a look at some of the flights available from Chicago to Boston departing last-minute. It's wise to confirm all flight details are correct before booking.

One-way flights from Chicago to Boston

The best deals found for one-way Chicago - Boston flights.

Users in need of a one-way flight from Chicago to Boston can choose from these deals. Users needing a return flight from Chicago to Boston should utilize the search form above.

Find flights from Chicago to Boston within your budget

Use the slider to find flights from Chicago to Boston that fit your budget.

Related info for your journey

See answers for the most popular questions asked about this flight route.

More flights from Chicago

More flights to Boston

More flights to Boston from Chicago

Find a rental car for your trip

Airlines that fly from Chicago to Boston

See the airlines flying to Boston from Chicago over the last 12 months, their prices and their punctuality.

What time of day do Chicago to Boston flights depart?

A summary of when current Chicago - Boston flight route schedules depart.

What days of the week do Chicago to Boston flights depart?

A summary of the days of the week where flights depart Chicago for Boston.

FAQs

How does Priceline get cheap flights? ›

What airline is not on Priceline? ›