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Boston Logan International Airport to Chicago flight

Search for flights from Boston Logan International Airport to Chicago and check out affordable one-way and round-trip options.

      • Cheapest nonstop
        BOS 20:50
        2h 54m
        Direct
        ORD 22:44
        Boston - Chicago | Wed, Aug 26 | Delta Air Lines
        ORD 19:30
        2h 30m
        Direct
        BOS 23:00
        Chicago - Boston | Wed, Sep 2 | Delta Air Lines
        S$ 162 S$ 202
        20% off
        20% off
        S$ 202 S$ 162
      • BOS 10:28
        3h 1m
        Direct
        ORD 12:29
        Boston - Chicago | Fri, Aug 21 | American Airlines
        MDW 06:40
        2h 15m
        Direct
        BOS 09:55
        Chicago - Boston | Fri, Aug 28 |
        S$ 170 S$ 202
        16% off
        16% off
        S$ 202 S$ 170
      • BOS 07:30
        2h 56m
        Direct
        ORD 09:26
        Boston - Chicago | Thu, Aug 13 | Delta Air Lines
        ORD 07:30
        2h 29m
        Direct
        BOS 10:59
        Chicago - Boston | Mon, Aug 17 | Delta Air Lines
        S$ 173 S$ 202
        14% off
        14% off
        S$ 202 S$ 173
      • BOS 07:30
        2h 56m
        Direct
        ORD 09:26
        Boston - Chicago | Fri, Aug 21 | Delta Air Lines
        ORD 07:30
        2h 29m
        Direct
        BOS 10:59
        Chicago - Boston | Mon, Aug 24 | Delta Air Lines
        S$ 174
        14% off
        S$ 202 S$ 174
      • BOS 20:50
        2h 54m
        Direct
        ORD 22:44
        Boston - Chicago | Wed, Aug 19 | Delta Air Lines
        ORD 10:30
        2h 29m
        Direct
        BOS 13:59
        Chicago - Boston | Sat, Aug 22 | Delta Air Lines
        S$ 174
        14% off
        S$ 202 S$ 174
      • BOS 20:50
        2h 54m
        Direct
        ORD 22:44
        Boston - Chicago | Sat, Aug 22 | Delta Air Lines
        ORD 19:30
        2h 30m
        Direct
        BOS 23:00
        Chicago - Boston | Fri, Aug 28 | Delta Air Lines
        S$ 175
        13% off
        S$ 202 S$ 175
      • BOS 07:30
        2h 56m
        Direct
        ORD 09:26
        Boston - Chicago | Fri, Aug 14 | Delta Air Lines
        ORD 10:30
        2h 29m
        Direct
        BOS 13:59
        Chicago - Boston | Fri, Aug 21 | Delta Air Lines
        S$ 177
        12% off
        S$ 202 S$ 177
      • BOS 06:14
        3h 6m
        Direct
        ORD 08:20
        Boston - Chicago | Sat, Aug 15 | American Airlines
        ORD 05:45
        2h 15m
        Direct
        BOS 09:00
        Chicago - Boston | Wed, Aug 19 |
        S$ 177
        12% off
        S$ 202 S$ 177
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Mon, Aug 10 | Normal Airline
        CHI 15:00
        6h
        Direct
        BOS 16:00
        Chicago - Boston | Wed, Aug 12 | Normal Airline
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      • Cheapest nonstop
        BOS 12:10
        2h 52m
        Direct
        ORD 14:02
        Boston - Chicago | Tue, Oct 6 | Delta Air Lines
        S$ 78 S$ 112
        30% off
        30% off
        S$ 112 S$ 78
      • BOS 18:50
        3h 4m
        Direct
        ORD 20:54
        Boston - Chicago | Sat, Sep 5 | Delta Air Lines
        S$ 93 S$ 112
        17% off
        17% off
        S$ 112 S$ 93
      • BOS 18:50
        3h 4m
        Direct
        ORD 20:54
        Boston - Chicago | Sat, Aug 29 | Delta Air Lines
        S$ 93 S$ 112
        17% off
        17% off
        S$ 112 S$ 93
      • BOS 20:50
        2h 54m
        Direct
        ORD 22:44
        Boston - Chicago | Tue, Aug 18 | Delta Air Lines
        S$ 96
        14% off
        S$ 112 S$ 96
      • BOS 07:30
        2h 56m
        Direct
        ORD 09:26
        Boston - Chicago | Sat, Aug 22 | Delta Air Lines
        S$ 96
        14% off
        S$ 112 S$ 96
      • BOS 19:17
        3h 18m
        Direct
        ORD 21:35
        Boston - Chicago | Sat, Sep 5 | American Airlines
        S$ 98
        13% off
        S$ 112 S$ 98
      • BOS 13:00
        17h 25m
        1 stop
        CHI 14:00
        Boston - Chicago | Mon, Aug 10 | Normal Airline
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Trip.com Price Insights: Flights from Boston Logan International Airport to Chicago

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

The data is based on Trip.com data from the past 12 months and shows the average one-way fares by month from Boston Logan International Airport to Chicago.

Based on Trip.com data from the past 12 months, the cheapest one-way flights from Boston Logan International Airport to Chicago are usually in August, with an average price of S$ 155. October sees the highest fares, around S$ 253.

S$ 253
S$ 204
S$ 155
S$ 106
  • S$ 155
    Aug
  • S$ 190
    Sep
  • S$ 253
    Oct
  • S$ 218
    Nov
  • S$ 164
    Dec
  • S$ 161
    Jan
  • S$ 200
    Feb
  • S$ 204
    Mar
  • S$ 193
    Apr
  • S$ 170
    May
  • S$ 173
    Jun
  • S$ 192
    Jul

Which day of the week has the cheapest flights from Boston Logan International Airport to Chicago?

The data is based on Trip.com data from the past 12 months and shows the average fares by each day of the week from Boston Logan International Airport to Chicago.

Based on Trip.com data from the past 12 months, the cheapest day for flights from Boston Logan International Airport to Chicago is Tuesday, with average prices lower than other days. Try to avoid departing on Sunday, as fares are typically the highest.

S$ 243
S$ 198
S$ 153
S$ 108
  • S$ 172
    Mon
  • S$ 153
    Tue
  • S$ 178
    Wed
  • S$ 203
    Thu
  • S$ 204
    Fri
  • S$ 186
    Sat
  • S$ 243
    Sun

Selected Airlines from Boston Logan International Airport to Chicago

See which airlines fly from Boston Logan International Airport to Chicago. Find the airline that best meets your travel needs by comparing prices and treat yourself to an enjoyable journey.
Delta Air Lines logo Delta Air Lines

Flight Schedule from Boston Logan International Airport to Chicago

Check the schedule for flights from Boston Logan International Airport to Chicago and find the flight that best matches your travel plans.

Flight info.
Departure
Arrival
Weekly Schedule

  1. DL2816

    Boston Logan International Airport

    12:25

    BOS

    2h 54m

    14:19

    ORD

    S M T W T - S
    Search

  2. DL2570

    Boston Logan International Airport

    07:30

    BOS

    2h 56m

    09:26

    ORD

    S M T W T F S
    Search

  3. AA3048

    Boston Logan International Airport

    12:05

    BOS

    3h 2m

    14:07

    ORD

    S M T W T F S
    Search

  4. DL2804

    Boston Logan International Airport

    20:10

    BOS

    2h 54m

    22:04

    ORD

    S M T W T F S
    Search

  5. AA3324

    Boston Logan International Airport

    06:00

    BOS

    3h 10m

    08:10

    ORD

    S M T W T F S
    Search

  6. AA1479

    Boston Logan International Airport

    16:29

    BOS

    3h 13m

    18:42

    ORD

    S M T W T F S
    Search

  7. AA3160

    Boston Logan International Airport

    19:17

    BOS

    3h 18m

    21:35

    ORD

    S M T W T F S
    Search

  8. F93511

    Boston Logan International Airport

    12:56

    BOS

    2h 55m

    Direct

    15:51

    ATL

    S M T W T F S
    Search

  9. F92779

    Hartsfield–Jackson Atlanta International Airport

    10:05

    ATL

    2h 2m

    Direct

    11:07

    MDW

    S M T W T F S

  10. F93511

    Boston Logan International Airport

    12:56

    BOS

    2h 55m

    Direct

    15:51

    ATL

    S M T W T F S
    Search

  11. F91595

    Hartsfield–Jackson Atlanta International Airport

    18:23

    ATL

    2h 30m

    Direct

    19:53

    ORD

    S - - W T - S

  12. F93511

    Boston Logan International Airport

    12:56

    BOS

    2h 55m

    Direct

    15:51

    ATL

    S M T W T F S
    Search

  13. F93397

    Hartsfield–Jackson Atlanta International Airport

    18:23

    ATL

    2h 30m

    Direct

    19:53

    ORD

    - M T - - F -
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Flight Info of Flights from Boston Logan International Airport to Chicago

Cheapest return ticket price S$ 170
Cheapest one-way flight price S$ 78
Off-season for travel October
Peak season for travel July

FAQs for Boston Logan International Airport to Chicago Flights

Popular Destinations & Recommendations

Note: Prices shown on this page are the lowest estimated 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 shown before payment. Charges for checked baggage, meals, Wi-Fi, and other optional services may also appear in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page have been updated within the last 24 hours, and with many routes refreshed in real time. The more popular the route, the more accurate 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.