Cheap flights from Chicago (CHI) to Boston (BOS) from $33

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/27. 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
Jun 4 — Jun 111

The best prices from Chicago to Boston Logan Intl are usually found in January or February, 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 May 30, 2024.

Popular in

June

Cheapest in

January

Round-trip from

$218

One-way from

$79
High demand for flights, 15% potential price rise
Best time to find cheap flights, 25% 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 51 days in advance to save up to 42% 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 51 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 $263, or $346 for flights within the next 24 hours.

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

January is one of the best times of the year to fly to Boston from Chicago. Prices for January average $268 per person but you can even find prices for as low as $99. The most expensive prices can be found in the month of June. Opting for a January flight can save you 18% on your journey compared to booking in June

What is the cheapest time of day to fly from CHI to BOS?

It’s typically best to fly out from Chicago to Boston in the evening. Doing so could potentially save you 19% on the flight price compared to flying at noon, which is usually more expensive.

Cheap Spirit Airlines flights from Chicago to Boston

Explore cheap flight options specifically provided by Spirit 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 2,784,634 searches. Data last updated May 30, 2024.
Find some of the cheapest Spirit 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.
Tue 8/279:04 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Wed 8/287:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 5/29$33
Tue 8/279:04 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Wed 8/287:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 5/29$40
Tue 6/119:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Wed 6/126:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/30$41
Tue 8/279:04 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Wed 8/2811:16 amBOS - ORD
1 stop10h 08mSpirit Airlines
Deal found 5/29$46
Fri 9/69:04 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Tue 9/107:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 5/28$50
Wed 9/119:04 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Wed 9/257:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 5/28$51
Tue 8/276:00 amORD - BOS
1 stop13h 55mSpirit Airlines
Wed 8/287:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 5/29$53
Tue 6/119:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Wed 6/196:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/30$58
Tue 8/209:04 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Tue 8/277:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 5/30$60
  • If you’re traveling from Chicago to Boston, one of the more common airlines traveling that route is Spirit Airlines. Chicago to Boston flights are typically 10% cheaper than other airlines traveling the same route. Flights from Spirit Airlines typically cost $328.65 RT. The cheapest Spirit Airlines flight found for this route was $63. 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 11% more popular than any other airline flying that same route.

Cheap JetBlue flights from Chicago to Boston

Explore cheap flight options specifically provided by JetBlue 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 2,784,634 searches. Data last updated May 30, 2024.
Some of the best deals we've found on JetBlue flights traveling from Chicago to Boston. Make sure to examine the flight information before completing your reservation.
Tue 6/117:30 pmORD - BOS
Nonstop2h 26mJetBlue
Tue 6/186:00 amBOS - ORD
Nonstop2h 54mJetBlue
Deal found 5/29$160
Thu 6/1310:35 amORD - BOS
1 stop8h 32mJetBlue
Sun 6/166:00 amBOS - ORD
Nonstop2h 54mJetBlue
Deal found 5/29$166
Fri 8/308:33 pmORD - BOS
Nonstop2h 26mJetBlue
Mon 9/26:00 amBOS - ORD
Nonstop2h 54mJetBlue
Deal found 5/29$183
Fri 7/58:33 pmORD - BOS
Nonstop2h 26mJetBlue
Wed 7/106:00 amBOS - ORD
Nonstop2h 54mJetBlue
Deal found 5/29$187
Tue 6/47:15 pmORD - BOS
Nonstop2h 26mJetBlue
Wed 6/55:45 amBOS - ORD
1 stop5h 11mJetBlue
Deal found 5/28$189
Sat 6/810:43 amORD - BOS
1 stop5h 56mJetBlue
Mon 6/175:50 pmBOS - ORD
Nonstop2h 57mJetBlue
Deal found 5/30$213
  • JetBlue is one of the most popular airlines used for those traveling from Chicago to Boston. Flights from JetBlue traveling this route typically cost $147.79 RT. This price is typically 109% 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, JetBlue flights are 11% more popular than any other airline flying that same route.

Cheap Chicago to Boston flights in May & June 2024

Find cheap flight options from Chicago to Boston specifically for the months of May and June 2024. Explore affordable fares based on user searches. Over the last 7 days, Cheapflights users made 2,784,634 searches. Prices were last updated on May 30, 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.
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Wed 6/129:18 amBOS - MDW
1 stop14h 40mFrontier
Deal found 5/29$124
Thu 6/68:51 pmMDW - BOS
1 stop10h 25mFrontier
Mon 6/107:49 amBOS - MDW
1 stop6h 49mFrontier
Deal found 5/29$125
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Wed 6/129:16 amBOS - MDW
1 stop25h 15mFrontier
Deal found 5/30$126
Tue 6/119:37 pmORD - BOS
3 stops17h 34mSpirit Airlines
Fri 6/1411:28 amBOS - ORD
1 stop7h 44mSpirit Airlines
Deal found 5/29$140
Thu 6/139:37 pmORD - BOS
2 stops15h 48mSpirit Airlines
Sun 6/166:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/29$141
Thu 6/207:13 pmORD - BOS
1 stop12h 03mMultiple Airlines
Wed 6/266:30 amBOS - ORD
Nonstop2h 54mMultiple Airlines
Deal found 5/29$142
Wed 6/55:05 amORD - BOS
2 stops16h 55mSpirit Airlines
Sun 6/96:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/29$143
Thu 6/135:21 amORD - BOS
1 stop10h 34mSpirit Airlines
Mon 6/176:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/29$144
Sun 6/99:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Tue 6/118:00 pmBOS - ORD
2 stops15h 01mSpirit Airlines
Deal found 5/29$145

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 2,784,634 searches. Data last updated May 30, 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 8/317:59 pmMDW - BOS
1 stop10h 26mFrontier
Tue 9/312:36 pmBOS - MDW
1 stop7h 37mFrontier
Deal found 5/29$116
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Wed 6/129:18 amBOS - MDW
1 stop14h 40mFrontier
Deal found 5/29$124
Thu 6/68:51 pmMDW - BOS
1 stop10h 25mFrontier
Mon 6/107:49 amBOS - MDW
1 stop6h 49mFrontier
Deal found 5/29$125
Tue 6/1110:16 pmMDW - BOS
1 stop7h 42mFrontier
Wed 6/129:16 amBOS - MDW
1 stop25h 15mFrontier
Deal found 5/30$126
Thu 6/135:07 pmORD - BOS
1 stop20h 18mSpirit Airlines
Wed 6/193:42 pmBOS - ORD
1 stop6h 05mSpirit Airlines
Deal found 5/30$139
Mon 7/19:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Tue 7/93:42 pmBOS - ORD
1 stop6h 05mSpirit Airlines
Deal found 5/29$140
Thu 6/139:37 pmORD - BOS
2 stops15h 48mSpirit Airlines
Sun 6/166:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/29$141
Thu 6/207:13 pmORD - BOS
1 stop12h 03mMultiple Airlines
Wed 6/266:30 amBOS - ORD
Nonstop2h 54mMultiple Airlines
Deal found 5/29$142
Sat 7/202:02 pmORD - BOS
1 stop9h 25mMultiple Airlines
Thu 7/252:54 pmBOS - ORD
1 stop7h 04mMultiple Airlines
Deal found 5/29$143

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 2,784,634 searches. Data last updated May 30, 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.
Tue 8/279:04 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Wed 8/287:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 5/29$33
Tue 8/279:04 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Wed 8/287:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 5/29$40
Tue 6/119:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Wed 6/126:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/30$41
Fri 9/69:04 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Tue 9/107:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 5/28$50
Wed 9/119:04 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Wed 9/257:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 5/28$51
Thu 6/139:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Mon 6/176:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/28$53
Tue 6/119:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Wed 6/196:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/30$58
Tue 8/209:04 pmORD - BOS
Nonstop2h 18mSpirit Airlines
Tue 8/277:00 amBOS - ORD
Nonstop2h 33mSpirit Airlines
Deal found 5/30$60
Fri 6/149:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Sun 6/166:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/29$61

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 2,784,634 searches. Data last updated May 30, 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.
Wed 6/58:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Wed 6/126:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/29$40
Wed 6/58:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Mon 6/176:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/29$61
Tue 6/49:35 amORD - BOS
1 stop11h 01mSpirit Airlines
Wed 6/56:10 amBOS - ORD
1 stop12h 30mSpirit Airlines
Deal found 5/28$70
Wed 6/58:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Wed 6/1212:07 pmBOS - ORD
1 stop7h 58mSpirit Airlines
Deal found 5/29$72
Wed 6/58:02 pmORD - BOS
Nonstop2h 29mSpirit Airlines
Sat 6/156:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/29$73
Sun 6/99:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Tue 6/116:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/29$75
Fri 6/79:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Tue 6/116:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/29$77
Wed 6/511:01 amORD - BOS
1 stop10h 59mSpirit Airlines
Tue 6/186:30 amBOS - ORD
Nonstop2h 54mSpirit Airlines
Deal found 5/29$79
Thu 6/65:01 amORD - BOS
1 stop5h 29mMultiple Airlines
Tue 6/116:30 amBOS - ORD
Nonstop2h 54mMultiple Airlines
Deal found 5/28$81

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 2,784,634 searches. Data last updated May 30, 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.
Wed 8/217:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 5/30$64
Thu 6/68:51 pmMDW - BOS
1 stop10h 25mFrontier
Deal found 5/30$68
Thu 6/68:51 pmMDW - BOS
1 stop10h 25mFrontier
Deal found 5/29$69
Tue 8/277:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 5/30$72
Wed 8/147:59 pmMDW - BOS
1 stop10h 26mFrontier
Deal found 5/29$74
Sat 7/66:00 amORD - BOS
Nonstop2h 22mUnited Airlines
Deal found 5/29$79
Fri 7/58:00 amORD - BOS
Nonstop2h 34mDelta
Deal found 5/29$80
Tue 6/119:19 amORD - BOS
2 stops13h 56mSpirit Airlines
Deal found 5/30$81
Sun 6/239:10 pmORD - BOS
Nonstop2h 28mSpirit Airlines
Deal found 5/29$82

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 2,784,634 searches. Data last updated May 30, 2024.

Fly from

Any airport

Fly to

Any airport

Budget

$33 - $160

Route

Depart

Return

Price

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 8/27

Nonstop2h 18m

Boston Logan Intl

Wed 8/28

Nonstop2h 33m

$33

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 8/27

Nonstop2h 18m

Boston Logan Intl

Wed 8/28

Nonstop2h 33m

$40

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 6/11

Nonstop2h 28m

Boston Logan Intl

Wed 6/12

Nonstop2h 54m

$41

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 8/27

Nonstop2h 18m

Boston Logan Intl

Wed 8/28

1 stop10h 08m

$46

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Fri 9/6

Nonstop2h 18m

Boston Logan Intl

Tue 9/10

Nonstop2h 33m

$50

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/11

Nonstop2h 18m

Boston Logan Intl

Wed 9/25

Nonstop2h 33m

$51

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Wed 9/18

1 stop5h 45m

Boston Logan Intl

Sat 9/28

Nonstop2h 33m

$95

Chicago MidwayBoston Logan Intl

MDW - BOS

MDWBOS

Chicago Midway

Thu 6/6

1 stop10h 25m

Boston Logan Intl

Mon 6/10

1 stop6h 49m

$146

Chicago O'Hare IntlBoston Logan Intl

ORD - BOS

ORDBOS

Chicago O'Hare Intl

Tue 6/11

Nonstop2h 26m

Boston Logan Intl

Tue 6/18

Nonstop2h 54m

$160

Flights are sorted by cheapest first

Deals found on 5/29

How far ahead should I 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 May 24, 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

What is the cheapest day 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 May 26, 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

Best time to book a flight from Chicago to Boston

Have a flexible travel schedule? Discover the best time to fly to Boston from Chicago with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

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 May 30, 2024.
Peruse reviews from past customers who have flown with Spirit Airlines, JetBlue and Southwest 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
5,956 reviews

Food

7.3

Entertainment

7.8

Overall

8.2

Boarding

8.3

Comfort

8.1

Crew

8.7

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

Southwest
8.2
Very good
5,956 reviews
Southwest
8.2
Very good
5,956 reviews

Food

7.3

Entertainment

7.8

Overall

8.2

Boarding

8.3

Comfort

8.1

Crew

8.7

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

8.0
Very good
10,457 reviews
Southwest
8.2
Very good
5,956 reviews

Food

7.3

Entertainment

7.8

Overall

8.2

Boarding

8.3

Comfort

8.1

Crew

8.7

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

7.6
Good
4,365 reviews
Southwest
8.2
Very good
5,956 reviews

Food

7.3

Entertainment

7.8

Overall

8.2

Boarding

8.3

Comfort

8.1

Crew

8.7

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

7.4
Good
394 reviews
Southwest
8.2
Very good
5,956 reviews

Food

7.3

Entertainment

7.8

Overall

8.2

Boarding

8.3

Comfort

8.1

Crew

8.7

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

7.4
Good
10,777 reviews
Southwest
8.2
Very good
5,956 reviews

Food

7.3

Entertainment

7.8

Overall

8.2

Boarding

8.3

Comfort

8.1

Crew

8.7

Reviews

1 / 10

Wish the there were an electrical outlet to plug the phone. it died within 10 minutes of being in the air.

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 8 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 Spirit Airlines for just $33, but on average you can expect to pay $58.

  • Are there nonstop flights from Chicago to Boston for under $100 on Cheapflights?

    Cheapflights has at least 20 direct flights from Chicago to Boston under $100. A good price for a nonstop flight from Chicago to Boston is less than $60.

  • Are there last-minute flights available from Chicago to Boston for under $100?

    There are currently 20+ open flights from Chicago to Boston within the next 7 days for less than $100.

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

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

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

    On average, you can expect to see 51 flights from Chicago to Boston a day.
    Early Morning (Midnight to 6am) - 6% of flight departures
    Morning (6am - Noon) - 31% of flight departures
    Afternoon (Noon - 6pm) - 39% of flight departures
    Evening (6pm - Midnight) - 24% of flight departures

  • How long is the flight from Chicago to Boston?

    A quick flight from Chicago to Boston can take about 2h 18m. Spirit Airlines provides one of the quickest options available for as low as $33. Airlines will cover a distance of 869 mi. Generally, flights for this route are nonstop.

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

    Cheapflights users have booked flights from Chicago to Boston round-trip from $33. This flight start at 87% 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 Frontier. According to our data, you can fly for as low as $64. Users have also found prices from $79 and $80 on United Airlines and Delta, respectively.

  • 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: Republic Airways (93%), Envoy Air (91%), EL AL( 89%).

  • What are the cheapest flights from Chicago to Boston?

    On average you can expect to pay $1,008 for a flight from Chicago to Boston. The cheapest flight overall is $76 while the most popular route, (Chicago O'Hare Intl - Boston Logan Intl) is currently priced at $40.

  • 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.

  • Can I find deals for flights from Chicago to Boston that include extra baggage allowance?

    The amount of baggage you can bring on your Chicago to Boston flight depends on the airline and the type of fare you've chosen. After entering your flight details, you'll be able to view the specific baggage policies for each deal in the search results. Keep in mind that certain deals may offer additional baggage allowance.

  • Can I find deals on flights from Chicago to Boston with specific airlines?

    Yes, Cheapflights allows you to browse and filter Chicago to Boston flight deals by airline. After entering your origin and destination, use the available filters to view flights offered by airlines.

  • Can I find deals for flights from Chicago to Boston that include hotel bookings?

    Yes. In addition to deals on Chicago to Boston flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Chicago to Boston?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Chicago to Boston.

  • Can I find deals for business class flights from Chicago to Boston?

    Yes. Cheapflights offers flight deals from Chicago to Boston by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • Can I find deals for flights from Chicago to Boston that allow pets onboard?

    Many airlines flying from Chicago to Boston offer the option to travel with pets. After selecting a flight deal, you can find more information about the airline's pet policy on their official website or by contacting the airline directly. Please note that additional fees and restrictions may apply.

  • Can I find deals on last-minute flights from Chicago to Boston?

    Yes, you can often find last-minute deals on Chicago to Boston flights on Cheapflights. However, these deals can vary and may not always be available. We recommend checking back frequently or signing up for price alerts for the most up-to-date deals.

  • How recently were the Chicago to Boston flight deals updated?

    The Chicago to Boston flight deals you see on this page were last updated on 5/30.

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

  • What is the cheapest month to book a flight from Chicago to Boston?

    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 July 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.

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 May 30, 2024.

Top 7 airlines flying from Chicago to Boston

Discover the top 7 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 2,784,634 searches. Data last updated May 30, 2024.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$58Average$149FlexibilityNo cancel feeOn-time65%
Search Spirit Airlines flights
DeltaCheapest$63Average$329FlexibilityNo cancel feeOn-timeN/A
Search Delta flights
Alaska AirlinesCheapest$69Average$148FlexibilityNo cancel feeOn-time75%
Search Alaska Airlines flights
JetBlueCheapest$71Average$223FlexibilityNo cancel feeOn-time62%
Search JetBlue flights
United AirlinesCheapest$84Average$318FlexibilityNo cancel feeOn-time69%
Search United Airlines flights
FrontierCheapest$84Average$168FlexibilityNo cancel feeOn-time62%
Search Frontier flights
American AirlinesCheapest$118Average$279FlexibilityNo cancel feeOn-time71%
Search American 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 May 30, 2024.
3%of flight departuresEarly morningMidnight to 6 am
41%of flight departuresMorning6 am to noon
42%of flight departuresAfternoonNoon to 6 pm
14%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 May 30, 2024.
Sunday60daily flights
Monday65daily flights
Tuesday57daily flights
Wednesday57daily flights
Thursday60daily flights
Friday58daily flights
Saturday44daily flights

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travelers can enjoy low prices and a wide availability of flights to their desired destinations.

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.

100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.