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Flights from Boston to Chicago

Cheapest airlines flights from Boston to Chicago

You can choose from 4 airlines that fly from Boston to Chicago, including American Airlines, Jetblue Airways, and United Airlines. Jetblue Airways has lowest fares on this route.
American Airlines logo American Airlines
Jetblue Airways logo Jetblue Airways
United Airlines logo United Airlines
Delta Air Lines logo Delta Air Lines
Airlines are determined based on actual purchased flight tickets from Boston to Chicago according to previous 12 months data from Trip.com.

Search for direct flights from Boston to Chicago in the next 3 months. Based on Trip.com's latest 7-day flight data, one-way direct flights start at US$50, and round-trip direct flights start at US$85.

      • Cheapest nonstop
        BOS 06:05
        3h 3m
        Nonstop
        ORD 08:08
        Boston - Chicago | Wed, Apr 8 | Jetblue Airways
        ORD 06:50
        2h 21m
        Nonstop
        BOS 10:11
        Chicago - Boston | Mon, Apr 13 | Delta Air Lines
        US$85 US$148
        43% off
        43% off
        US$148 US$85
      • BOS 07:15
        3h 10m
        Nonstop
        ORD 09:25
        Boston - Chicago | Wed, Apr 8 | Delta Air Lines
        ORD 19:35
        2h 27m
        Nonstop
        BOS 23:02
        Chicago - Boston | Wed, Apr 8 | Delta Air Lines
        US$93 US$148
        37% off
        37% off
        US$148 US$93
      • BOS 06:05
        3h 3m
        Nonstop
        ORD 08:08
        Boston - Chicago | Tue, Apr 7 | Jetblue Airways
        ORD 10:15
        2h 20m
        Nonstop
        BOS 13:35
        Chicago - Boston | Tue, Apr 14 | Delta Air Lines
        US$95 US$148
        36% off
        36% off
        US$148 US$95
      • BOS 07:15
        3h 10m
        Nonstop
        ORD 09:25
        Boston - Chicago | Tue, Apr 7 | Delta Air Lines
        ORD 19:59
        2h 28m
        Nonstop
        BOS 23:27
        Chicago - Boston | Tue, Apr 14 | Delta Air Lines
        US$96
        35% off
        US$148 US$96
      • BOS 18:48
        3h 12m
        Nonstop
        ORD 21:00
        Boston - Chicago | Tue, Apr 7 | American Airlines
        ORD 19:59
        2h 28m
        Nonstop
        BOS 23:27
        Chicago - Boston | Tue, Apr 14 | Delta Air Lines
        US$96
        35% off
        US$148 US$96
      • BOS 08:03
        3h 9m
        Nonstop
        ORD 10:12
        Boston - Chicago | Wed, Apr 8 | American Airlines
        ORD 17:39
        2h 33m
        Nonstop
        BOS 21:12
        Chicago - Boston | Wed, Apr 8 | American Airlines
        US$97
        34% off
        US$148 US$97
      • BOS 19:35
        3h 4m
        Nonstop
        ORD 21:39
        Boston - Chicago | Sat, Apr 25 | Jetblue Airways
        ORD 06:00
        2h 26m
        Nonstop
        BOS 09:26
        Chicago - Boston | Sat, May 2 | Delta Air Lines
        US$98
        34% off
        US$148 US$98
      • BOS 06:30
        3h 14m
        Nonstop
        ORD 08:44
        Boston - Chicago | Sat, May 2 | American Airlines
        ORD 19:59
        2h 28m
        Nonstop
        BOS 23:27
        Chicago - Boston | Tue, May 5 | Delta Air Lines
        US$98
        34% off
        US$148 US$98
      • BOS 19:35
        3h 1m
        Nonstop
        ORD 21:36
        Boston - Chicago | Sat, May 9 | Jetblue Airways
        ORD 19:15
        2h 34m
        Nonstop
        BOS 22:49
        Chicago - Boston | Tue, May 12 | Delta Air Lines
        US$98
        34% off
        US$148 US$98
      • BOS 19:40
        3h 10m
        Nonstop
        ORD 21:50
        Boston - Chicago | Sat, Apr 11 | American Airlines
        ORD 06:50
        2h 21m
        Nonstop
        BOS 10:11
        Chicago - Boston | Mon, Apr 13 | Delta Air Lines
        US$133
        10% off
        US$148 US$133
      • BOS 13:00
        17h 25m
        1 stop
        CHI Invalid Date
        Boston - Chicago | Mon, Mar 16 | Normal Airline
        CHI 15:00
        6h
        Nonstop
        BOS 16:00
        Chicago - Boston | Wed, Mar 18 | Normal Airline
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      • Cheapest nonstop
        BOS 06:05
        3h 3m
        Nonstop
        ORD 08:08
        Boston - Chicago | Sat, Apr 11 | Jetblue Airways
        US$50 US$68
        26% off
        26% off
        US$68 US$50
      • BOS 20:20
        2h 56m
        Nonstop
        ORD 22:16
        Boston - Chicago | Mon, Mar 23 | Delta Air Lines
        US$54 US$68
        21% off
        21% off
        US$68 US$54
      • BOS 07:15
        3h 10m
        Nonstop
        ORD 09:25
        Boston - Chicago | Tue, Apr 7 | Delta Air Lines
        US$56 US$68
        18% off
        18% off
        US$68 US$56
      • BOS 17:35
        3h 17m
        Nonstop
        ORD 19:52
        Boston - Chicago | Tue, Apr 7 | American Airlines
        US$57
        16% off
        US$68 US$57
      • BOS 19:40
        3h 10m
        Nonstop
        ORD 21:50
        Boston - Chicago | Mon, Apr 13 | American Airlines
        US$58
        15% off
        US$68 US$58
      • BOS 07:10
        3h
        Nonstop
        ORD 09:10
        Boston - Chicago | Tue, Apr 7 | Jetblue Airways
        US$58
        15% off
        US$68 US$58
      • BOS 07:35
        2h 52m
        Nonstop
        ORD 09:27
        Boston - Chicago | Wed, May 13 | Delta Air Lines
        US$58
        15% off
        US$68 US$58
      • BOS 07:35
        2h 52m
        Nonstop
        ORD 09:27
        Boston - Chicago | Sun, May 10 | Delta Air Lines
        US$59
        13% off
        US$68 US$59
      • BOS 06:52
        2h 59m
        Nonstop
        ORD 08:51
        Boston - Chicago | Sun, May 10 | Jetblue Airways
        US$59
        13% off
        US$68 US$59
      • BOS 13:00
        17h 25m
        1 stop
        CHI Invalid Date
        Boston - Chicago | Mon, Mar 16 | Normal Airline
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Displayed flight fares from Boston to Chicago are based on average prices across airlines for the next 3 months, according to the latest Trip.com database.

Boston to Chicago Flight Details

The distance between Boston and Chicago is about 1,371.27 km. The average flying time from Boston to Chicago is around 3 hours 3 minutes. Based on Trip.com's latest data, travel demand is highest in July. The off-season for travel is October.

Cheapest one-way flight priceUS$50
Cheapest return ticket priceUS$85
Cheapest monthOctober
Peak season for travelJuly
Flight distance1,371.27 km
Average flight time3 hours 3 minutes
Popular airlineAmerican Airlines
Flight statistics for the Boston–Chicago route are based on aggregated booking data from Trip.com over the past 12 months.

Trip.com Price Insights on Flights from Boston to Chicago

Which month has the cheapest one-way flights from Boston to Chicago?

The average price of one-way flights from Boston to Chicago purchased by Trip.com users by month over the past 12 months.

Based on Trip.com’s data, the cheapest month for flights from Boston to Chicago is March, with an average price of US$122; while the month with the highest flight price is usually October, with an average price of up to US$193.

US$193
US$158
US$122
US$87
  • US$122
    Mar
  • US$162
    Apr
  • US$153
    May
  • US$161
    Jun
  • US$177
    Jul
  • US$122
    Aug
  • US$146
    Sep
  • US$193
    Oct
  • US$167
    Nov
  • US$126
    Dec
  • US$123
    Jan
  • US$153
    Feb

What is the cheapest day of the week to fly from Boston to Chicago?

Average weekly flight prices from Boston to Chicago by travel date (Based on Trip.com’s past 12 months of data)

Based on Trip.com’s past 12 months of flight data, the cheapest day to fly from Boston to Chicago is Tuesday, with average prices lower than on other days. Avoid Sunday, as prices are usually highest then.

US$185
US$149
US$113
US$77
  • US$142
    Mon
  • US$113
    Tue
  • US$154
    Wed
  • US$160
    Thu
  • US$168
    Fri
  • US$144
    Sat
  • US$185
    Sun

What is the cheapest day to fly from Boston to Chicago during Easter Day?

Based on Trip.com's data over the past 3 days, these are the lowest one-way flight prices from Boston to Chicago during Easter Day.

During the Easter Day period, the cheapest flights from Boston to Chicago were available on Apr 13 with the lowest price being US$78.

US$118
US$98
US$78
US$58
    Cheapest
  • US$92
    Apr 8
  • US$118
    Apr 9
  • US$102
    Apr 10
  • US$79
    Apr 11
  • US$108
    Apr 12
  • US$78
    Apr 13
  • US$85
    Apr 14

Frequently Asked Questions

  • What are the cheapest flights from Boston to Chicago (BOS-CHI)?

    Based on Trip.com data, Jetblue Airways offers one-way fares as low as US$50 on Cheapest nonstop routes (e.g. BOS to ORD on Sat, Apr 11), while Jetblue Airways offers Cheapest nonstop round-trips from US$85 departing on Wed, Apr 8 and returning on Mon, Apr 13.
  • At the moment, you can catch a nonstop flight from Boston to Chicago with the following airlines, including: Jetblue Airways American Airlines United Airlines Delta Air Lines Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.
  • It takes about 3 hours 3 minutes to fly from Boston to Chicago.
  • By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Boston to Chicago is around 40 days (6 weeks) in advance, and the best time to fly is usually on Tuesday, Wednesday, and Saturday. Tuesday typically offers the cheapest flights for departure, while Saturday offers the best return deals.
  • Based on Trip.com data in the past 4 weeks, there is 98 flight per week flying from Boston to Chicago. You can check the weekly schedule for popular airlines on this route below: United Airlines: S/M/T/W/T/F/S -- UA2488 (07:30) United Airlines: S/M/T/W/T/F/S -- UA1349 (08:29)
  • To find best deals on flights from Boston to Chicago, you can use various tools on Trip.com:
    · Be flexible with your travel dates to get the cheapest flight deal. Now the cheapest flight deal is on Sat, Apr 11, with one-way flights priced at just US$50.
    · Compare airlines strategically. Budget carriers often provide the lowest base fares, while we found the most affordable airline currently operating on this route is Jetblue Airways.
    · Set up price alerts to easily monitor ticket prices without having to check every day.
    · Check Trip.com flight deals and promo codes frequently.
    · Avoid peak season unless you book very early. It seems the peak season for Chicago travel is around July.
    · Get exclusive promo codes for Trip.com app users.
  • The cheapest months to fly from Boston to Chicago is October, when demand for travel is lower.
  • After crunching the numbers on our March flight calendar, it's currently cheapest to fly from Boston to Chicago on March 31, 2026 with Delta Air Lines, with prices starting at US$50.
  • You can land at any one of the following hubs in Chicago, with Logan International Airport to O'Hare International Airport (BOS-ORD) is by far the most common option on this route: Midway International Airport (MDW) O'Hare International Airport (ORD) Chicago Rockford International Airport (RFD).
  • The time difference between Chicago and Boston is 1h.
  • Tickets can only be changed or canceled if permitted by airline policy. To submit a change or cancellation request, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and segment, and submit a request. Please note that additional charges may apply according to the airline ticket policy. However, if the flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For more details about change and cancellation policies, please check the customer support pages.

Trip.com Airline Insights on Flights from Boston to Chicago

Which airline offers the cheapest direct flights from Boston to Chicago?

Data is based on the average price of all nonstop flights from Boston to Chicago on Trip.com over the past 12 months.

Based on Trip.com’s data from the past 12 months, Jetblue Airways provides the lowest-priced direct flights from Boston to Chicago, with fares starting at US$142.

US$118
US$142
US$166
US$190
US$214
Jetblue Airways
US$142
Jetblue Airways
Delta Air Lines
US$155
Delta Air Lines
American Airlines
US$163
American Airlines
United Airlines
US$195
United Airlines
Spirit Airlines
US$214
Spirit Airlines

Which airline operates the most flights from Boston to Chicago?

Total flights from Boston to Chicago across all airlines. (Based on Trip.com data from the past month)

Based on Trip.com’s data from the past month, American Airlines operates the most frequent flights from Boston to Chicago, with 58 flights per week.

3
21
40
58
American Airlines
58
American Airlines
United Airlines
41
United Airlines
Air New Zealand
39
Air New Zealand
All Nippon Airways
26
All Nippon Airways
Delta Air Lines
24
Delta Air Lines
Japan Airlines
21
Japan Airlines

How many flights fly from Boston to Chicago daily?

The data is based on the flight numbers for each day of the week from Boston to Chicago within the Trip.com database over the past month.

Based on the past month's historical data from Trip.com, the number of flights from Boston to Chicago is the highest on Friday and the lowest on Tuesday.

280
223
165
108
Highest
172
Mon
165
Tue
205
Wed
225
Thu
280
Fri
215
Sat
250
Sun

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Note: Prices shown on this page are the estimated lowest prices found in the last 24 hours and include all taxes and fees.

Book with no extra fees

Prices displayed on this page are all-inclusive (incl. taxes, fuel surcharges, Civil Aviation Development Fund, etc.), and all fees are clearly shown before you pay. Charges for checked baggage, onboard meals, Wi‑Fi, and other optional services are also included where applicable in the flight cards.

Real-time pricing updates

Prices, availability, and travel details on this page have been updated within the last 24 hours, and for many routes are refreshed in real time. The more popular the route, the more accurate and up-to-date the data.

Change & Cancellation Policy

Trip.com shows the change and cancellation rules for each ticket during the booking process, including all related fees and conditions. Please refer to the following scenarios:
Voluntary cancellation/change:
To request a change or cancellation, go to the flight bookings page, select the option to change or cancel your booking, choose the relevant passengers and flight segment, and submit your request. Please note that additional charges may apply based on the airline’s fare rules.
Cancellation/change due to a flight schedule change:
If your flight has been rescheduled and you would like to change or cancel your ticket, you can submit an involuntary cancellation request. For full details of change and cancellation policies, please refer to the customer support pages.