Trip.com
>
Flights
>
Flights to United States
>
Flights to Mississippi
>
Flights to Tupelo
>
Chicago to Tupelo Regional Airport flight

Explore the cheapest one-way and round-trip flights from Chicago to Tupelo Regional Airport over the next 90 days, with one-way fares from £156 and round-trip from £342. Based on Trip.com's latest 7-day flight data.

      • ORD 6:56 AM
        5h 24m
        1 stop
        TUP 12:20 PM
        Chicago - Tupelo | Fri, Sep 25 | American Airlines
        TUP 7:45 AM
        4h 52m
        1 stop
        ORD 12:37 PM
        Tupelo - Chicago | Sun, Sep 27 | Contour Airlines
        £342 £546
        37% off
        37% off
        £546 £342
      • ORD 1:20 PM
        22h 50m
        1 stop
        TUP 12:10 PM
        Chicago - Tupelo | Tue, Oct 20 | American Airlines
        TUP 8:00 AM
        14h
        1 stop
        ORD 10:00 PM
        Tupelo - Chicago | Fri, Oct 23 | Contour Airlines
        £354 £546
        35% off
        35% off
        £546 £354
      • ORD 11:00 PM
        13h 20m
        1 stop
        TUP 12:20 PM
        Chicago - Tupelo | Sat, Sep 26 | American Airlines
        TUP 7:45 AM
        23h 29m
        1 stop
        ORD 7:14 AM
        Tupelo - Chicago | Tue, Sep 29 | Contour Airlines
        £354 £546
        35% off
        35% off
        £546 £354
      • ORD 6:55 AM
        5h 15m
        1 stop
        TUP 12:10 PM
        Chicago - Tupelo | Tue, Oct 20 | United Airlines
        TUP 8:00 AM
        25h 32m
        1 stop
        ORD 9:32 AM
        Tupelo - Chicago | Fri, Oct 23 | Contour Airlines
        £362
        34% off
        £546 £362
      • ORD 7:00 AM
        5h 20m
        1 stop
        TUP 12:20 PM
        Chicago - Tupelo | Fri, Sep 25 | United Airlines
        TUP 7:45 AM
        6h 52m
        1 stop
        ORD 2:37 PM
        Tupelo - Chicago | Sun, Sep 27 | Contour Airlines
        £363
        34% off
        £546 £363
      • ORD 3:40 PM
        20h 40m
        1 stop
        TUP 12:20 PM
        Chicago - Tupelo | Sat, Sep 26 | United Airlines
        TUP 7:45 AM
        25h 47m
        1 stop
        ORD 9:32 AM
        Tupelo - Chicago | Tue, Sep 29 | Contour Airlines
        £363
        34% off
        £546 £363
      • ORD 6:59 AM
        5h 11m
        1 stop
        TUP 12:10 PM
        Chicago - Tupelo | Wed, Oct 21 | American Airlines
        TUP 8:00 AM
        14h
        1 stop
        ORD 10:00 PM
        Tupelo - Chicago | Mon, Oct 26 | Contour Airlines
        £388
        28% off
        £546 £388
      • ORD 6:55 AM
        5h 15m
        1 stop
        TUP 12:10 PM
        Chicago - Tupelo | Wed, Oct 21 | United Airlines
        TUP 8:00 AM
        3h 34m
        1 stop
        ORD 11:34 AM
        Tupelo - Chicago | Mon, Oct 26 | Contour Airlines
        £398
        27% off
        £546 £398
      • ORD 1:24 PM
        22h 46m
        1 stop
        TUP 12:10 PM
        Chicago - Tupelo | Mon, Nov 9 | American Airlines
        TUP 8:00 AM
        13h 59m
        1 stop
        ORD 9:59 PM
        Tupelo - Chicago | Fri, Nov 13 | Contour Airlines
        £427
        22% off
        £546 £427
      • ORD 6:59 AM
        5h 11m
        1 stop
        TUP 12:10 PM
        Chicago - Tupelo | Mon, Nov 9 | United Airlines
        TUP 8:00 AM
        23h 56m
        1 stop
        ORD 7:56 AM
        Tupelo - Chicago | Fri, Nov 13 | Contour Airlines
        £434
        21% off
        £546 £434
      • ORD 6:56 AM
        5h 14m
        1 stop
        TUP 12:10 PM
        Chicago - Tupelo | Mon, Oct 5 | American Airlines
        TUP 8:00 AM
        23h 19m
        1 stop
        ORD 7:19 AM
        Tupelo - Chicago | Fri, Oct 9 | Contour Airlines
        £436
        20% off
        £546 £436
      • ORD 11:00 PM
        13h 10m
        1 stop
        TUP 12:10 PM
        Chicago - Tupelo | Tue, Oct 6 | American Airlines
        TUP 8:00 AM
        23h 19m
        1 stop
        ORD 7:19 AM
        Tupelo - Chicago | Tue, Oct 13 | Contour Airlines
        £442
        19% off
        £546 £442
      • CHI 1:00 PM
        17h 25m
        1 stop
        TUP 2:00 PM
        Chicago - Tupelo | Fri, Sep 25 | Normal Airline
        TUP 3:00 PM
        6h
        Nonstop
        CHI 4:00 PM
        Tupelo - Chicago | Sun, Sep 27 | Normal Airline
        Find more flights
        Find more flights
      • ORD 9:20 PM
        21h 25m
        1 stop
        TUP 6:45 PM
        Chicago - Tupelo | Sat, Oct 3 | American Airlines
        £156 £318
        51% off
        51% off
        £318 £156
      • ORD 6:56 AM
        5h 24m
        1 stop
        TUP 12:20 PM
        Chicago - Tupelo | Thu, Sep 24 | American Airlines
        £163 £318
        49% off
        49% off
        £318 £163
      • ORD 6:56 AM
        5h 24m
        1 stop
        TUP 12:20 PM
        Chicago - Tupelo | Sat, Sep 26 | American Airlines
        £168 £318
        47% off
        47% off
        £318 £168
      • ORD 6:56 AM
        5h 14m
        1 stop
        TUP 12:10 PM
        Chicago - Tupelo | Fri, Oct 2 | American Airlines
        £174
        45% off
        £318 £174
      • ORD 8:40 AM
        3h 40m
        1 stop
        TUP 12:20 PM
        Chicago - Tupelo | Sat, Sep 26 | United Airlines
        £179
        44% off
        £318 £179
      • ORD 9:20 PM
        15h
        1 stop
        TUP 12:20 PM
        Chicago - Tupelo | Tue, Sep 29 | American Airlines
        £180
        43% off
        £318 £180
      • ORD 8:40 AM
        3h 30m
        1 stop
        TUP 12:10 PM
        Chicago - Tupelo | Sat, Oct 3 | United Airlines
        £182
        43% off
        £318 £182
      • ORD 6:55 AM
        5h 15m
        1 stop
        TUP 12:10 PM
        Chicago - Tupelo | Fri, Oct 2 | United Airlines
        £183
        42% off
        £318 £183
      • ORD 6:59 AM
        5h 11m
        1 stop
        TUP 12:10 PM
        Chicago - Tupelo | Mon, Oct 5 | American Airlines
        £188
        41% off
        £318 £188
      • ORD 6:59 AM
        5h 11m
        1 stop
        TUP 12:10 PM
        Chicago - Tupelo | Tue, Oct 20 | American Airlines
        £189
        41% off
        £318 £189
      • ORD 6:55 AM
        5h 15m
        1 stop
        TUP 12:10 PM
        Chicago - Tupelo | Tue, Oct 20 | United Airlines
        £194
        39% off
        £318 £194
      • ORD 6:56 AM
        5h 24m
        1 stop
        TUP 12:20 PM
        Chicago - Tupelo | Mon, Sep 28 | American Airlines
        £257
        19% off
        £318 £257
      • CHI 1:00 PM
        17h 25m
        1 stop
        TUP 2:00 PM
        Chicago - Tupelo | Fri, Sep 25 | Normal Airline
        Find more flights
        Find more flights

Displayed flight fares from Chicago to Tupelo Regional Airport are based on average prices across airlines for the next 3 months, according to the latest Trip.com database.

Flight Schedule from Chicago to Tupelo Regional Airport

Flight info.
Departure
Arrival
Weekly Schedule

  1. UA1674

    O'Hare Intl. Airport

    8:40 AM

    ORD

    1h 50m

    Nonstop

    10:30 AM

    BNA

    - - - W T F -
    Search

  2. LF3002

    Nashville International Airport

    11:15 AM

    BNA

    1h 5m

    Nonstop

    12:20 PM

    TUP

    S - T W T F -

  3. UA2142

    O'Hare Intl. Airport

    2:15 PM

    ORD

    1h 24m

    Nonstop

    3:39 PM

    BNA

    S M T W T F S
    Search

  4. LF3004

    Nashville International Airport

    5:40 PM

    BNA

    1h 5m

    Nonstop

    6:45 PM

    TUP

    - - - - - - S

  5. UA2073

    O'Hare Intl. Airport

    6:55 AM

    ORD

    1h 45m

    Nonstop

    8:40 AM

    BNA

    - - - W T F -
    Search

  6. LF3002

    Nashville International Airport

    11:15 AM

    BNA

    1h 5m

    Nonstop

    12:20 PM

    TUP

    S - T W T F -

  7. AA2991

    O'Hare Intl. Airport

    1:53 PM

    ORD

    1h 36m

    Nonstop

    3:29 PM

    BNA

    S M T W T F S
    Search

  8. LF3004

    Nashville International Airport

    5:40 PM

    BNA

    1h 5m

    Nonstop

    6:45 PM

    TUP

    - - - - - - S

  9. AA3973

    O'Hare Intl. Airport

    6:44 AM

    ORD

    1h 42m

    Nonstop

    8:26 AM

    BNA

    S M T W T F S
    Search

  10. LF3002

    Nashville International Airport

    11:15 AM

    BNA

    1h 5m

    Nonstop

    12:20 PM

    TUP

    S - T W T F -

  11. DL5305

    Chicago Midway International Airport

    9:29 AM

    MDW

    1h 11m

    Nonstop

    11:40 AM

    DTW

    S M T W T F S
    Search

  12. DL1041

    Detroit Metropolitan Wayne County Airport

    12:45 PM

    DTW

    3h

    Nonstop

    2:45 PM

    DFW

    S M T W T F S

  13. LF3008

    Dallas Fort Worth International Airport

    5:00 PM

    DFW

    1h 45m

    Nonstop

    6:45 PM

    TUP

    S M T W T F -

  14. DL2840

    O'Hare Intl. Airport

    8:55 AM

    ORD

    1h 26m

    Nonstop

    11:21 AM

    DTW

    S M T W T F S
    Search

  15. DL1041

    Detroit Metropolitan Wayne County Airport

    12:45 PM

    DTW

    3h

    Nonstop

    2:45 PM

    DFW

    S M T W T F S

  16. LF3008

    Dallas Fort Worth International Airport

    5:00 PM

    DFW

    1h 45m

    Nonstop

    6:45 PM

    TUP

    S M T W T F -

  17. DL1285

    Chicago Midway International Airport

    6:00 AM

    MDW

    2h

    Nonstop

    9:00 AM

    ATL

    S M T W T F S
    Search

  18. DL1155

    Hartsfield–Jackson Atlanta International Airport

    9:40 AM

    ATL

    1h 14m

    Nonstop

    9:54 AM

    BNA

    S M T W T F S

  19. LF3004

    Nashville International Airport

    5:40 PM

    BNA

    1h 5m

    Nonstop

    6:45 PM

    TUP

    - - - - - - S

  20. DL2028

    O'Hare Intl. Airport

    6:00 AM

    ORD

    1h 30m

    Nonstop

    7:30 AM

    MSP

    S M T W T F S
    Search

  21. DL2970

    Minneapolis-Saint Paul International Airport

    10:10 AM

    MSP

    2h 41m

    Nonstop

    12:51 PM

    DFW

    S M T W T F S

  22. LF3008

    Dallas Fort Worth International Airport

    5:00 PM

    DFW

    1h 45m

    Nonstop

    6:45 PM

    TUP

    S M T W T F -

  23. UA314

    O'Hare Intl. Airport

    9:36 PM

    ORD

    1h 49m

    Nonstop

    11:25 PM

    BNA

    - - - W T F -
    Search

  24. LF3002

    Nashville International Airport

    11:15 AM

    BNA

    1h 5m

    Nonstop

    12:20 PM

    TUP

    S - T W T F -
Find more flights and airlines

What to know about flights from Chicago to Tupelo Regional Airport?

Cheapest one-way flight price£156
Off-season for travelAugust
Peak season for travelJune

FAQs for Chicago to Tupelo Regional Airport Flights

  • When are flight tickets from Chicago (CHI) to Tupelo (TUP) the cheapest?

    Airlines adjust prices for flights from Chicago to Tupelo based on the departure date and time of your selection. By analyzing data from all airlines, we've discovered that on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.
  • According to Trip.com's data, the lowest price is around £374.
  • One-way flights from Chicago to Tupelo Regional Airport currently start from £156, and round-trip fares start from £342. The lowest fare is currently available on flights operated by American Airlines departing on Sat, Oct 3. Fares are subject to change based on availability.
  • Enter your Chicago and Tupelo Regional Airport, select your departure date and number of passengers, then compare flights by price, flight duration and baggage allowance. Once you've chosen a fare, review the change and cancellation policy, fill in your passenger details and pay to receive your booking confirmation.

Popular Destinations

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

Book with no extra fees

Prices displayed in this page are all-inclusive prices (incl. taxes, fuel surcharge, civil aviation development fund, etc) with all fees confirmed before payment. Fees for luggage, meals, WLAN, or other additional services are also included as shown in the flight cards.

Real-time pricing updates

Prices, availability, and travel information on this page were updated within last 26 hours—even in real-time. The more popular the route, the more precise the data.

Change & Cancellation Policy

Trip.com displays flight cancellation and change policies for each flight ticket during the booking process, including fees and applicable conditions. Please check the following scenarios:
Voluntary cancellation/change:
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.
Cancellation/change due to a flight schedule change:
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.