Flight INFO & Delta Air Lines(DL) flights from Chicago to Boston

Cheapest one-way flight price US$86
Cheapest return ticket price US$163
Cheapest month August
Peak season for travel January
Flight distance 1,371.27 km
Average flight time 2 hours 31 minutes
Popular airline American Airlines
Frequency ～212/week

Book Delta Air Lines(DL) flights from Chicago to Boston

  • One way
  • Round-trip
      • direct cheapest
        ORD07:25
        2h 35m
        Nonstop
        BOS11:00
        Chicago - Boston|Tue, Nov 3|Delta Air Lines
        US$86
        US$213
        60% off
        Search
        60% off
        US$213
        US$86
      • ORD12:00
        2h 32m
        Nonstop
        BOS15:32
        Chicago - Boston|Thu, Nov 5|Delta Air Lines
        US$86
        US$213
        60% off
        Search
        60% off
        US$213
        US$86
      • ORD15:05
        2h 39m
        Nonstop
        BOS18:44
        Chicago - Boston|Mon, Oct 26|Delta Air Lines
        US$94
        US$213
        56% off
        Search
        56% off
        US$213
        US$94
      • ORD16:40
        2h 41m
        Nonstop
        BOS20:21
        Chicago - Boston|Wed, Nov 4|Delta Air Lines
        US$95
        Search
        US$95
      • ORD19:10
        2h 43m
        Nonstop
        BOS22:53
        Chicago - Boston|Tue, Oct 13|Delta Air Lines
        US$102
        Search
        US$102
      • ORD15:00
        2h 31m
        Nonstop
        BOS18:31
        Chicago - Boston|Wed, Oct 21|Delta Air Lines
        US$104
        Search
        US$104
      • ORD15:00
        2h 31m
        Nonstop
        BOS18:31
        Chicago - Boston|Tue, Oct 20|Delta Air Lines
        US$104
        Search
        US$104
      • ORD15:05
        2h 39m
        Nonstop
        BOS18:44
        Chicago - Boston|Tue, Oct 27|Delta Air Lines
        US$106
        Search
        US$106
      • ORD07:25
        2h 35m
        Nonstop
        BOS11:00
        Chicago - Boston|Sat, Oct 24|Delta Air Lines
        US$119
        Search
        US$119
      • ORD19:10
        2h 43m
        Nonstop
        BOS22:53
        Chicago - Boston|Fri, Oct 30|Delta Air Lines
        US$130
        Search
        US$130
      • ORD16:40
        2h 41m
        Nonstop
        BOS20:21
        Chicago - Boston|Sat, Oct 31|Delta Air Lines
        US$131
        Search
        US$131
      • ORD07:00
        2h 28m
        Nonstop
        BOS10:28
        Chicago - Boston|Fri, Nov 6|Delta Air Lines
        US$133
        Search
        US$133
      • ORD19:10
        2h 43m
        Nonstop
        BOS22:53
        Chicago - Boston|Fri, Oct 16|Delta Air Lines
        US$141
        Search
        US$141
      • ORD19:10
        2h 43m
        Nonstop
        BOS22:53
        Chicago - Boston|Wed, Oct 28|Delta Air Lines
        US$143
        Search
        US$143
      • ORD07:25
        2h 35m
        Nonstop
        BOS11:00
        Chicago - Boston|Sun, Nov 1|Delta Air Lines
        US$153
        Search
        US$153
      • ORD17:29
        5h 30m
        1 stops
        BOS23:59
        Chicago - Boston|Tue, Nov 3|Delta Air Lines
        US$90
        Search
        US$90
      • MDW16:19
        5h 55m
        1 stops
        BOS23:14
        Chicago - Boston|Tue, Nov 3|Delta Air Lines
        US$90
        Search
        US$90
      • MDW06:04
        6h 40m
        1 stops
        BOS13:44
        Chicago - Boston|Mon, Oct 26|Delta Air Lines
        US$98
        Search
        US$98
      • ORD07:00
        6h 25m
        1 stops
        BOS14:25
        Chicago - Boston|Thu, Nov 5|Delta Air Lines
        US$103
        Search
        US$103
      • MDW18:44
        4h 15m
        1 stops
        BOS23:59
        Chicago - Boston|Fri, Oct 30|Delta Air Lines
        US$136
        Search
        US$136
      • ORD06:10
        7h 39m
        1 stops
        BOS14:49
        Chicago - Boston|Fri, Oct 16|Delta Air Lines
        US$145
        Search
        US$145
      • MDW18:44
        4h 15m
        1 stops
        BOS23:59
        Chicago - Boston|Fri, Oct 16|Delta Air Lines
        US$145
        Search
        US$145
      • MDW18:44
        4h 15m
        1 stops
        BOS23:59
        Chicago - Boston|Thu, Nov 5|Delta Air Lines
        US$145
        Search
        US$145
      • ORD13:55
        4h 58m
        1 stops
        BOS19:53
        Chicago - Boston|Tue, Oct 13|Delta Air Lines
        US$147
        Search
        US$147
      • MDW13:27
        5h 26m
        1 stops
        BOS19:53
        Chicago - Boston|Tue, Oct 13|Delta Air Lines
        US$147
        Search
        US$147
      • MDW17:09
        7h 11m
        1 stops
        BOS01:20
        Chicago - Boston|Wed, Oct 28|Delta Air Lines
        US$147
        Search
        US$147
      • ORD11:30
        5h
        1 stops
        BOS17:30
        Chicago - Boston|Wed, Oct 28|Delta Air Lines
        US$148
        Search
        US$148
      • ORD17:29
        5h 30m
        1 stops
        BOS23:59
        Chicago - Boston|Sat, Oct 31|Delta Air Lines
        US$155
        Search
        US$155
      • MDW10:01
        7h 57m
        1 stops
        BOS18:58
        Chicago - Boston|Sat, Oct 31|Delta Air Lines
        US$155
        Search
        US$155
      • ORD12:30
        5h 24m
        1 stops
        BOS18:54
        Chicago - Boston|Sat, Oct 24|Delta Air Lines
        US$155
        Search
        US$155
      • CHI13:00
        5h 24m
        Nonstop
        BOS14:00
        Chicago - Boston|Mon, Sep 6|Normal Airline
        More cheap flights
        More cheap flights

Delta Air Lines(DL) flights from Chicago to Boston & Flight Schedule

Flight info.
Departure
Arrival
Weekly Schedule

  1. DL2570

    Delta Air Lines

    10:24

    ORD

    2.5h

    Nonstop

    13:54

    BOS

    S M T W T F S
    Search

  2. DL2828

    Delta Air Lines

    07:00

    ORD

    2.5h

    Nonstop

    10:28

    BOS

    S M T W T F S
    Search

  3. DL2816

    Delta Air Lines

    15:05

    ORD

    2.6h

    Nonstop

    18:44

    BOS

    S M T W T - S
    Search

  4. DL2646

    Delta Air Lines

    19:30

    ORD

    2.6h

    Nonstop

    23:09

    BOS

    S M T W T F S
    Search

  5. DL2251

    Delta Air Lines

    08:36

    ORD

    2.4h

    Nonstop

    11:59

    LGA

    S M T W T - -
    Search

  6. DL5758

    Delta Air Lines

    13:00

    LGA

    1.3h

    Nonstop

    14:20

    BOS

    S M T W T - S
    Search

  7. DL2985

    Delta Air Lines

    11:30

    ORD

    2.3h

    Nonstop

    14:49

    LGA

    S M T W T - S
    Search

  8. DL5819

    Delta Air Lines

    16:00

    LGA

    1.4h

    Nonstop

    17:25

    BOS

    S M T W T - S
    Search

  9. DL4714

    Delta Air Lines

    17:31

    MDW

    1.7h

    Nonstop

    19:15

    MSP

    S M T W T F S
    Search

  10. DL2614

    Delta Air Lines

    20:00

    MSP

    2.9h

    Nonstop

    23:53

    BOS

    S M T W T F S
    Search

  11. DL1063

    Delta Air Lines

    10:59

    MDW

    1.9h

    Nonstop

    13:53

    ATL

    S M T W T F S
    Search

  12. DL2595

    Delta Air Lines

    15:10

    ATL

    2.6h

    Nonstop

    17:48

    BOS

    S M T W T F S
    Search

  13. DL2358

    Delta Air Lines

    17:29

    ORD

    1.5h

    Nonstop

    20:00

    DTW

    S M T W T F S
    Search

  14. DL1187

    Delta Air Lines

    21:35

    DTW

    2.0h

    Nonstop

    23:34

    BOS

    S M T W T F S
    Search

  15. DL1728

    Delta Air Lines

    17:25

    MDW

    2.0h

    Nonstop

    20:26

    ATL

    S M T W T F S
    Search

  16. DL2987

    Delta Air Lines

    20:05

    ATL

    2.6h

    Nonstop

    22:41

    BOS

    S M T W T - S
    Search
Show less

Delta Air Lines(DL) flights from Chicago to Boston Flight Booking FAQ

  • Which airlines offer direct flights from Chicago to Boston?

    At the moment, you can catch a nonstop flight from Chicago to Boston with the following airlines, including: American Airlines Delta Air Lines Jetblue Airways United Airlines Selected airlines are based on historical data collected from flight bookings users made on Trip.com within the last 90 days.

  • How long is a flight from Chicago to Boston?

    It takes about 2 hours 31 minutes to fly from Chicago to Boston.

  • When is the best time to book flights from Chicago to Boston?

    By analyzing data from all airlines on the Trip.com flight calendar, it looks like the best time to book a flight from Chicago to Boston 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.

  • How many flights are there per week from Chicago to Boston?

    Based on Trip.com data in the past 4 weeks, there is 102 flight per week flying from Chicago to Boston. You can check the weekly schedule for popular airlines on this route below: United Airlines: S/M/T/W/T/F/S -- UA1606 (10:59)

  • When are flight tickets from Chicago (CHI) to Boston (BOS) the cheapest?

    The cheapest months to fly from Chicago to Boston is August, when demand for travel is lower.

  • Which upcoming date is cheapest to fly from Chicago to Boston on?

    After crunching the numbers on our October flight calendar, it's currently cheapest to fly from Chicago to Boston on October 24, 2026 with Delta Air Lines, with prices starting at US$83.

  • Which airports fly into Boston from Chicago?

    You can land at any one of the following hubs in Boston: Hartford Barnes Airport (BNH), Boston Logan International Airport (BOS), and Portsmouth International Airport (PSM). Flying from O'Hare International Airport to Boston Logan International Airport (ORD-BOS) is by far the most common option on this route.

  • Is there any time difference between Chicago and Boston?

    The time difference between Boston and Chicago is 1h.

  • How do I change or cancel my ticket from Chicago to Boston?

    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.