Cheap flights from Chicago (CHI) to Boston (BOS) from $68

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/12. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
CHI — BOS
Mar 24 — Mar 311

The best prices from Chicago to Boston Logan Intl are usually found in February or January, booked 84 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

Cheap flight deals from Chicago to Boston

Discover tips and strategies to find the most affordable flight options for your journey from Chicago (CHI) to Boston (BOS). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated March 19, 2024.

Popular in

June

Cheapest in

February

Round-trip from

$218

One-way from

$84
High demand for flights, 26% potential price rise
Best time to find cheap flights, 37% potential price drop
From Chicago (CHI) to Boston Logan Intl
One-way flight from Chicago (CHI) to Boston Logan Intl

What is the cheapest day to fly round-trip from Chicago to Boston?

Flying to your destination on a Sunday can be more expensive, but this shouldn’t discourage you from finding affordable options to get to Boston. Check prices with Cheapflights to find a great deal for your trip.

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

Travelers have found it’s best to book a flight 33 days in advance to save up to 34% compared to booking the same week of travel. As your travel date approaches, the cost of this flight route may potentially increase. While opting to book 33 days out may not be an option for all, there are still additional ways to secure a deal in the near future. You might find a flight from Chicago to Boston 1-2 weeks in advance for as low as $228, or $316 for flights within the next 24 hours.

What is the cheapest month to fly from Chicago to Boston?

February is one of the best times of the year to fly to Boston from Chicago. Prices for February average $250 per person but you can even find prices for as low as $76. The most expensive prices can be found in the month of June. Opting for a February flight can save you 34% on your journey compared to booking in June

When is the cheapest time to fly from Chicago to Boston (CHI - BOS)?

It’s typically best to fly out from Chicago to Boston in the evening. Doing so could potentially save you 17% on the flight price compared to flying at noon, which is usually more expensive.

Cheap American Airlines flights from Chicago to Boston

Explore cheap flight options specifically provided by American Airlines for the route between Chicago and Boston. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 3,145,932 searches. Data last updated March 19, 2024.
Find some of the cheapest American Airlines flights traveling from Chicago to Boston. Be sure to come back soon if the deals available don't appeal to you at this time.
Sat 5/113:20 pmORD - BOS
1 stop4h 40mAmerican Airlines
Tue 5/145:25 amBOS - ORD
Nonstop2h 56mAmerican Airlines
Deal found 3/18$170
Tue 4/235:12 pmORD - BOS
1 stop4h 54mAmerican Airlines
Tue 4/308:30 amBOS - ORD
Nonstop2h 58mAmerican Airlines
Deal found 3/18$183
Sat 4/63:34 pmORD - BOS
Nonstop2h 17mAmerican Airlines
Mon 4/86:10 pmBOS - ORD
1 stop5h 14mAmerican Airlines
Deal found 3/18$192
Wed 4/176:36 amORD - BOS
1 stop4h 02mAmerican Airlines
Tue 4/238:30 amBOS - ORD
Nonstop2h 58mAmerican Airlines
Deal found 3/18$193
Sat 3/308:35 pmORD - BOS
Nonstop2h 19mAmerican Airlines
Thu 4/46:00 amBOS - ORD
1 stop6h 11mAmerican Airlines
Deal found 3/18$207
Mon 3/257:30 amORD - BOS
1 stop5h 11mAmerican Airlines
Wed 4/105:50 amBOS - ORD
1 stop6h 24mAmerican Airlines
Deal found 3/18$217
Fri 3/298:35 pmORD - BOS
Nonstop2h 19mAmerican Airlines
Sun 3/317:40 amBOS - ORD
1 stop4h 38mAmerican Airlines
Deal found 3/18$218
Wed 3/274:42 pmORD - BOS
1 stop5h 13mAmerican Airlines
Sat 3/306:00 amBOS - ORD
1 stop5h 26mAmerican Airlines
Deal found 3/18$226
Thu 3/288:45 amORD - BOS
1 stop4h 17mAmerican Airlines
Fri 3/297:10 amBOS - ORD
1 stop6h 30mAmerican Airlines
Deal found 3/18$228
  • If you’re traveling from Chicago to Boston, one of the more common airlines traveling that route is American Airlines. Flights from American Airlines traveling this route typically cost $233.90 RT. This price is typically 73% more expensive than other airlines that offer Chicago to Boston flights. When booking this route, the cheapest RT price found was $69. The most popular departure airport in Chicago when flying to Boston is Chicago O'Hare Intl Airport. The most popular airport to fly into when visiting Boston is Boston Logan Intl Airport. When flying from Chicago to Boston, American Airlines flights are 9% more popular than any other airline flying that same route.

Cheap Delta flights from Chicago to Boston

Explore cheap flight options specifically provided by Delta for the route between Chicago and Boston. Find affordable fares and compare prices with other airlines to secure the best deal for your journey. Over the last 7 days, Cheapflights users made 3,145,932 searches. Data last updated March 19, 2024.
Some of the best deals we've found on Delta flights traveling from Chicago to Boston. Make sure to examine the flight information before completing your reservation.
Wed 5/156:25 amORD - BOS
Nonstop2h 29mDelta
Wed 5/152:10 pmBOS - ORD
Nonstop2h 53mDelta
Deal found 3/18$172
Fri 4/56:25 amORD - BOS
Nonstop2h 22mDelta
Wed 4/106:25 amBOS - ORD
Nonstop2h 56mDelta
Deal found 3/18$173
Wed 4/176:15 amORD - BOS
Nonstop2h 20mDelta
Wed 4/246:25 amBOS - ORD
Nonstop2h 56mDelta
Deal found 3/18$174
Wed 5/228:05 pmORD - BOS
Nonstop2h 35mDelta
Sat 8/245:40 pmBOS - ORD
Nonstop3h 00mDelta
Deal found 3/18$178
Tue 4/236:15 amORD - BOS
Nonstop2h 20mDelta
Fri 4/266:25 amBOS - ORD
Nonstop2h 56mDelta
Deal found 3/18$208
Fri 4/56:25 amORD - BOS
Nonstop2h 22mDelta
Wed 4/1012:59 pmBOS - ORD
1 stop6h 36mDelta
Deal found 3/18$241
Fri 3/291:14 pmMDW - BOS
1 stop5h 50mDelta
Sun 3/315:25 amBOS - MDW
1 stop4h 21mDelta
Deal found 3/18$316
Tue 3/267:59 pmORD - BOS
Nonstop2h 23mDelta
Thu 3/286:15 amBOS - ORD
Nonstop3h 08mDelta
Deal found 3/18$328
  • One of the most popular airlines traveling from Chicago to Boston is Delta. Flights from Delta traveling this route typically cost $317.80 RT. This price is typically 54% cheaper than other airlines that offer Chicago to Boston flights. When booking this route, the cheapest RT price found was $89. Chicago O'Hare Intl Airport is the most common Chicago airport to take off from when flying to Boston. Boston Logan Intl Airport is the most popular arrival airport in Boston. When flying from Chicago to Boston, Delta flights are 8% more popular than any other airline flying that same route.

Cheap Chicago to Boston flights in March & April 2024

Find cheap flight options from Chicago to Boston specifically for the months of March and April 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 3,145,932 searches. Prices were last updated on March 19, 2024.
Check out some of the best flight deals from Chicago to Boston in 2024. More deals are always being added, so be sure to check back regularly.
Sat 4/138:17 pmMDW - BOS
1 stop10h 51mFrontier
Sat 4/2012:41 pmBOS - MDW
1 stop11h 00mFrontier
Deal found 3/18$98
Wed 4/38:05 amMDW - BOS
1 stop23h 40mFrontier
Tue 4/911:53 amBOS - MDW
1 stop6h 08mFrontier
Deal found 3/18$105
Wed 4/38:43 pmMDW - BOS
1 stop11h 02mFrontier
Wed 4/1012:46 pmBOS - MDW
1 stop11h 37mFrontier
Deal found 3/18$107
Sun 4/286:27 pmMDW - BOS
1 stop12h 41mFrontier
Wed 5/112:46 pmBOS - MDW
1 stop11h 44mFrontier
Deal found 3/18$108
Sun 4/285:51 pmORD - BOS
1 stop13h 17mFrontier
Wed 5/18:21 amBOS - ORD
1 stop27h 26mFrontier
Deal found 3/18$109
Tue 4/1612:53 pmMDW - BOS
1 stop17h 28mFrontier
Tue 4/2310:21 amBOS - MDW
1 stop14h 55mFrontier
Deal found 3/18$110
Sun 4/286:27 pmMDW - BOS
1 stop12h 41mFrontier
Mon 4/2912:41 pmBOS - MDW
1 stop11h 49mFrontier
Deal found 3/18$117
Fri 4/123:44 pmMDW - BOS
1 stop15h 24mFrontier
Wed 4/1712:46 pmBOS - MDW
1 stop11h 37mFrontier
Deal found 3/18$118
Tue 4/2311:47 amORD - BOS
1 stop28h 00mMultiple Airlines
Tue 4/3011:12 amBOS - ORD
1 stop6h 39mMultiple Airlines
Deal found 3/18$119

Chicago to Boston 2024 flight deals

Discover exclusive flight deals for travel between Chicago and Boston in 2024. Find excellent offers based on user searches. Over the last 7 days, Cheapflights users made 3,145,932 searches. Data last updated March 19, 2024.
Check out some of the best flight deals from Chicago to Boston in 2024. More deals are always being added, so be sure to check back regularly.
Thu 5/25:56 pmMDW - BOS
1 stop13h 12mFrontier
Sat 5/1112:41 pmBOS - MDW
1 stop11h 00mFrontier
Deal found 3/18$96
Sat 4/138:17 pmMDW - BOS
1 stop10h 51mFrontier
Sat 4/2012:41 pmBOS - MDW
1 stop11h 00mFrontier
Deal found 3/18$98
Thu 5/95:56 pmMDW - BOS
1 stop13h 12mFrontier
Mon 5/1312:41 pmBOS - MDW
1 stop11h 49mFrontier
Deal found 3/18$99
Wed 4/38:05 amMDW - BOS
1 stop23h 40mFrontier
Tue 4/911:53 amBOS - MDW
1 stop6h 08mFrontier
Deal found 3/18$105
Wed 4/38:43 pmMDW - BOS
1 stop11h 02mFrontier
Wed 4/1012:46 pmBOS - MDW
1 stop11h 37mFrontier
Deal found 3/18$107
Sun 4/286:27 pmMDW - BOS
1 stop12h 41mFrontier
Wed 5/112:46 pmBOS - MDW
1 stop11h 44mFrontier
Deal found 3/18$108
Sun 4/285:51 pmORD - BOS
1 stop13h 17mFrontier
Wed 5/18:21 amBOS - ORD
1 stop27h 26mFrontier
Deal found 3/18$109
Tue 4/1612:53 pmMDW - BOS
1 stop17h 28mFrontier
Tue 4/2310:21 amBOS - MDW
1 stop14h 55mFrontier
Deal found 3/18$110
Sun 4/286:27 pmMDW - BOS
1 stop12h 41mFrontier
Mon 4/2912:41 pmBOS - MDW
1 stop11h 49mFrontier
Deal found 3/18$117

Non-stop flights to Boston from Chicago

Discover non-stop flight options from Chicago to Boston. Find direct flights with no layovers, providing a convenient travel experience. Explore non-stop flight options based on user searches, and compare prices and availability for your desired travel dates. Over the last 7 days, Cheapflights users made 3,145,932 searches. Data last updated March 19, 2024.
To help reduce your travel time, choose from one of these non-stop flights from Chicago to Boston. Those looking to potentially save on 1 or 2-stop flights from Chicago to Boston should utilize the search form at the the top of the page.
Wed 5/88:28 amORD - BOS
Nonstop2h 29mJetBlue
Wed 5/84:35 pmBOS - ORD
Nonstop2h 55mJetBlue
Deal found 3/18$127
Wed 5/87:15 pmORD - BOS
Nonstop2h 26mJetBlue
Sat 5/114:35 pmBOS - ORD
Nonstop2h 55mJetBlue
Deal found 3/19$133
Sat 6/157:20 pmORD - BOS
Nonstop2h 25mJetBlue
Tue 6/186:45 amBOS - ORD
Nonstop2h 54mJetBlue
Deal found 3/18$137
Wed 4/246:10 pmORD - BOS
Nonstop2h 26mJetBlue
Sat 4/273:20 pmBOS - ORD
Nonstop2h 54mJetBlue
Deal found 3/19$139
Wed 5/87:15 pmORD - BOS
Nonstop2h 26mJetBlue
Mon 5/136:10 amBOS - ORD
Nonstop2h 54mJetBlue
Deal found 3/19$153
Fri 4/268:15 pmORD - BOS
Nonstop2h 32mDelta
Tue 4/302:15 pmBOS - ORD
Nonstop2h 49mDelta
Deal found 3/19$159
Tue 6/48:05 pmORD - BOS
Nonstop2h 35mDelta
Sat 6/811:00 amBOS - ORD
Nonstop2h 52mDelta
Deal found 3/18$163
Tue 4/28:38 amORD - BOS
Nonstop2h 29mJetBlue
Wed 4/36:00 amBOS - ORD
Nonstop2h 53mJetBlue
Deal found 3/18$167
Thu 5/28:15 pmORD - BOS
Nonstop2h 32mDelta
Tue 5/72:10 pmBOS - ORD
Nonstop2h 53mDelta
Deal found 3/19$168

Chicago to Boston flights leaving soon

Find last-minute flight options from Chicago to Boston for spontaneous travel. Discover available flights and compare prices based on user searches. Secure great deals and offers for spontaneous trips with quick booking options. Over the last 7 days, Cheapflights users made 3,145,932 searches. Data last updated March 19, 2024.
Have a look at some of the last-minute flights available departing from Chicago to Boston. Users should be sure to double check the price, date, and time of their last-minute flight.
Fri 3/298:43 pmMDW - BOS
1 stop11h 02mFrontier
Wed 4/38:21 amBOS - MDW
1 stop9h 40mFrontier
Deal found 3/18$151
Tue 3/265:58 pmORD - BOS
1 stop13h 47mMultiple Airlines
Tue 4/99:45 amBOS - ORD
1 stop14h 46mMultiple Airlines
Deal found 3/18$170
Wed 3/276:21 pmORD - BOS
1 stop13h 24mMultiple Airlines
Wed 4/33:56 pmBOS - ORD
1 stop9h 14mMultiple Airlines
Deal found 3/18$172
Tue 3/267:58 pmMDW - BOS
1 stop11h 47mFrontier
Tue 4/211:53 amBOS - MDW
1 stop6h 08mFrontier
Deal found 3/17$172
Wed 3/279:14 amORD - BOS
1 stop8h 23mSpirit Airlines
Tue 4/25:17 pmBOS - ORD
1 stop27h 35mSpirit Airlines
Deal found 3/17$174
Thu 3/286:21 pmORD - BOS
1 stop13h 24mMultiple Airlines
Tue 4/211:06 amBOS - ORD
1 stop22h 12mMultiple Airlines
Deal found 3/18$175
Wed 3/279:14 amORD - BOS
1 stop8h 23mMultiple Airlines
Tue 4/23:56 pmBOS - ORD
1 stop10h 44mMultiple Airlines
Deal found 3/17$176
Thu 3/286:21 pmORD - BOS
1 stop13h 24mFrontier
Tue 4/29:45 amBOS - ORD
1 stop16h 55mFrontier
Deal found 3/19$178
Fri 3/293:02 pmORD - BOS
1 stop16h 43mFrontier
Tue 4/29:45 amBOS - ORD
1 stop16h 55mFrontier
Deal found 3/18$181

One-way flights to Boston from Chicago

Search for one-way flight options from Chicago to Boston. Find affordable one-way fares based on user searches. Compare prices and availability to plan your one-way journey according to your preferred dates and budget. Over the last 7 days, Cheapflights users made 3,145,932 searches. Data last updated March 19, 2024.
Users traveling one-way from Chicago to Boston can select one of these great deals. Users in need of a round-trip flight from Chicago to Boston instead should update the search form at the top of page.
Fri 4/127:45 amORD - BOS
1 stop27h 46mSpirit Airlines
Deal found 3/17$68
Wed 5/156:08 pmMDW - BOS
1 stop12h 17mFrontier
Deal found 3/18$68
Tue 3/263:22 pmMDW - BOS
1 stop15h 09mFrontier
Deal found 3/18$69
Wed 4/2411:06 amORD - BOS
Nonstop2h 29mJetBlue
Deal found 3/18$70
Sun 4/76:26 pmMDW - BOS
1 stop13h 19mFrontier
Deal found 3/18$70
Wed 4/2412:10 pmORD - BOS
1 stop7h 35mSpirit Airlines
Deal found 3/18$71
Wed 5/297:57 pmMDW - BOS
1 stop10h 28mFrontier
Deal found 3/18$71
Thu 4/46:10 amORD - BOS
1 stop12h 34mSpirit Airlines
Deal found 3/17$72
Wed 5/155:32 pmORD - BOS
1 stop5h 49mJetBlue
Deal found 3/18$73

Find flights from Chicago to Boston within your budget

Customize your flight search to find flights from Chicago to Boston that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 3,145,932 searches. Data last updated March 19, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$96 - $205

Route

Depart

Return

Price

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

Thu 5/2

1 stop13h 12m

Boston Logan Intl

Sat 5/11

1 stop11h 00m

$96

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

Sat 4/13

1 stop10h 51m

Boston Logan Intl

Sat 4/20

1 stop11h 00m

$98

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

Thu 5/9

1 stop13h 12m

Boston Logan Intl

Mon 5/13

1 stop11h 49m

$99

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 4/23

1 stop28h 00m

Boston Logan Intl

Tue 4/30

1 stop6h 39m

$119

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 4/3

1 stop6h 31m

Boston Logan Intl

Mon 4/8

1 stop14h 51m

$120

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 5/8

Nonstop2h 29m

Boston Logan Intl

Wed 5/8

Nonstop2h 55m

$127

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Sat 5/11

1 stop4h 40m

Boston Logan Intl

Tue 5/14

Nonstop2h 56m

$170

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 5/15

Nonstop2h 29m

Boston Logan Intl

Wed 5/15

Nonstop2h 53m

$172

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 4/16

1 stop5h 41m

Boston Logan Intl

Fri 4/19

Nonstop2h 52m

$205

Flights are sorted by cheapest first

Deals found on 3/18

When is the best time to book a flight from Chicago to Boston?

Use this chart to determine the optimal time to book a round-trip flight from Chicago to Boston. Price data was last updated on January 28, 2024.
The price you pay for your flight from Chicago to Boston may vary depending on when you book. For the best chance of a lower fare, look to book 84 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Search Deals

When is the cheapest time to fly from Chicago to Boston?

Use this chart to determine the cheapest time to fly round-trip from Chicago to Boston. Price data was last updated on March 10, 2024.
Morning
Noon
Afternoon
Evening
All times are departure.
Travelers seeking maximum savings on their Chicago to Boston flight should consider departing on Wednesday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Search Deals

Average price of flights to Boston by month

Plan your trip from Chicago to Boston by taking into account the cheapest months to travel. The average price of a one-way flight from Chicago to Boston is currently $70 while a round-trip flight costs $134. Price data was last updated on March 10, 2024.

Currently, January is the cheapest month in which you can book a flight from Chicago to Boston (average of $218). Flying from Chicago to Boston in June is currently the most expensive (average of $328). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

January

$218

February

$219

March

$263

April

$293

May

$287

June

$328

July

$328

August

$284

September

$258

October

$262

November

$258

December

$233

Temperature and rainfall in Boston by month

Plan your trip to Boston by taking into account the average temperature and rainfall totals by month.

BOS

Temperature

30.2 - 73.4 °F

Reviews of airlines servicing Boston

Get insights into the airlines that provide service to Boston. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Boston. Reviews last updated March 19, 2024.
Peruse reviews from past customers who have flown with American Airlines, Delta and Frontier from Chicago to Boston to help guide your decision. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.2
Very good
6,382 reviews

Comfort

8.1

Entertainment

7.9

Food

7.4

Crew

8.8

Overall

8.2

Boarding

8.3

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Southwest
8.2
Very good
6,382 reviews
Southwest
8.2
Very good
6,382 reviews

Comfort

8.1

Entertainment

7.9

Food

7.4

Crew

8.8

Overall

8.2

Boarding

8.3

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

8.1
Very good
11,551 reviews
Southwest
8.2
Very good
6,382 reviews

Comfort

8.1

Entertainment

7.9

Food

7.4

Crew

8.8

Overall

8.2

Boarding

8.3

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

7.7
Good
4,921 reviews
Southwest
8.2
Very good
6,382 reviews

Comfort

8.1

Entertainment

7.9

Food

7.4

Crew

8.8

Overall

8.2

Boarding

8.3

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

7.4
Good
460 reviews
Southwest
8.2
Very good
6,382 reviews

Comfort

8.1

Entertainment

7.9

Food

7.4

Crew

8.8

Overall

8.2

Boarding

8.3

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

7.4
Good
11,602 reviews
Southwest
8.2
Very good
6,382 reviews

Comfort

8.1

Entertainment

7.9

Food

7.4

Crew

8.8

Overall

8.2

Boarding

8.3

Reviews

1 / 10

No tray tables for food or drink not convenient nor comfortable

Related info for your journey

Find useful and relevant information for your journey from Chicago to Boston. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
  • What airport do you fly into for flights to Boston from Chicago?

    Boston Logan Intl (BOS) is the airport you will fly into if you book a flight from Chicago to Boston. You should not have trouble finding flights to Logan Intl from Chicago; the airport handles an average of 57 inbound flights from Chicago per day. You should also have plenty of airline options to choose from since 7 airlines have flights to the Boston airport from Chicago. It is only a 2.6 mi journey from Logan Intl (BOS) to Boston’s city center.

  • Can I find flights from Chicago to Boston for under $100 on Cheapflights?

    Yes, there are multiple flights from Chicago to Boston for under $100. The cheapest flight booked recently is on Frontier for just $96, but on average you can expect to pay $114.

  • Are there nonstop flights from Chicago to Boston for under $200 on Cheapflights?

    Cheapflights has at least 20 direct flights from Chicago to Boston under $200. A good price for a nonstop flight from Chicago to Boston is less than $166.

  • Are there last-minute flights available from Chicago to Boston for under $200?

    There are currently 20+ open flights from Chicago to Boston within the next 7 days for less than $200.

  • What days are nonstop flights available from Chicago to Boston?

    Days when nonstop flights are available for this flight are: Tuesday, Friday, Saturday.

  • How many flights depart from Chicago to Boston on average per day?

    On average, you can expect to see 6 flights from Chicago to Boston a day.
    Morning (6am - Noon) - 50% of flight departures
    Afternoon (Noon - 6pm) - 50% of flight departures

  • How long is the flight from Chicago to Boston?

    A quick flight from Chicago to Boston can take about 2h 29m. Frontier provides one of the quickest options available for as low as $96. Airlines will cover a distance of 869 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Chicago to Boston round-trip?

    Cheapflights users have booked flights from Chicago to Boston round-trip from $96. Other airlines that can offer you cheap pricing are Spirit Airlines, from $120, and JetBlue, from $127. These flights start at 61% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Chicago to Boston one-way?

    For one-way options, check prices for Spirit Airlines. According to our data, you can fly for as low as $68. Users have also found prices from $68 and $70 on Frontier and JetBlue, respectively.

  • What are the most popular airlines that fly from Chicago to Boston?

  • What are the most reliable airlines from Chicago to Boston?

    Before booking your flight to Boston from Chicago, check out the most reliable airlines to get you to your destination on time: WestJet (100%), Air France (100%), China Eastern( 100%).

  • What are the cheapest flights from Chicago to Boston?

    On average you can expect to pay $475 for a flight from Chicago to Boston. The cheapest flight overall is $83 while the most popular route, (Chicago O'Hare Intl - Boston Logan Intl) is currently priced at $120.

  • What does ORD to BOS mean?

    This is defined as Chicago O'Hare Intl Airport (ORD) and Boston Logan Intl Airport (BOS). Codes like Boston Logan Intl Airport are often used to just call airports uniquely. Chicago Midway Airport (MDW), Chicago Greater Rockford Airport (RFD) are other airports near this flight route and their unique identifiers/IATA codes.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Fly from Chicago to Boston on these airlines
Choose from the following airlines for your flight from Chicago to Boston. Flights are based on user searches made on Cheapflights and were last updated on March 19, 2024.

Top 6 airlines flying from Chicago to Boston

Discover the top 6 airlines that operate flights from Chicago to Boston. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 3,145,932 searches. Data last updated March 19, 2024.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$64Average$208FlexibilityNo cancel feeOn-time62%
Search JetBlue flights
Alaska AirlinesCheapest$69Average$234FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines flights
United AirlinesCheapest$84Average$299FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
DeltaCheapest$89Average$318FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
American AirlinesCheapest$114Average$276FlexibilityNo cancel feeOn-time71%
Search American Airlines flights
Spirit AirlinesCheapest$130Average$194FlexibilityNo cancel feeOn-time65%
Search Spirit Airlines flights

Search flights from Chicago to Boston by cabin class

Find flights from Chicago to Boston, based on your preferred cabin class, be it economy, premium economy, business, or first class.

Hourly flight availability from Chicago to Boston

Find hourly flight availability from Chicago to Boston. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 19, 2024.
5%of flight departuresEarly morningMidnight to 6 am
38%of flight departuresMorning6 am to noon
37%of flight departuresAfternoonNoon to 6 pm
20%of flight departuresEvening6 pm to midnight
Midnight
6 AM
Noon
6 PM

Weekly flight availability from Chicago to Boston

Explore weekly flight availability from Chicago to Boston. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated March 19, 2024.
Sunday60daily flights
Monday65daily flights
Tuesday57daily flights
Wednesday57daily flights
Thursday60daily flights
Friday58daily flights
Saturday44daily flights

Fly with Cheapflights

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How does Cheapflights help users find flights from Chicago to Boston?

Cheapflights helps you search for flights from Chicago to Boston via 900+ travel sites so you don’t have to. After performing a flight search, users can also filter their flight selection by filtering for price, number of stops, airlines, and so on.

Why should you use Cheapflights to find cheap flight tickets from Chicago to Boston?

Cheapflights taps into our reliable network of hundreds of airlines and travel agencies to find the best deals for flights from Chicago to Boston for you. Better yet — we are completely free to use.

Can Cheapflights find flights from Chicago to Boston with no change fees?

Yes! Cheapflights helps users easily find flights from Chicago to Boston with no change fees.

Can Cheapflights notify me if prices for flights from Chicago to Boston become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Boston from Chicago today and book when prices fit your budget.

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