App
Customer Support
PHP
Find Bookings
Worldwide Coverage
Worldwide Coverage
Flights to over 5,000 cities
One-stop Service Guarantee
One-stop Service Guarantee
Price guaranteed upon confirmed payment, booking guaranteed once tickets issued
Secure Payment
Secure Payment
Convenient & reliable booking and payment system

Cheap flight deals from Tupelo to Chicago Starting at PHP 8,560

We've found these cheap flights for you. You can book one-way or round-trip flight tickets.

  • One way
  • Round-trip
      • TUP07:45 am
        6h 47m
        1 stop
        ORD02:32 pm
        Tue, Feb 25|Tupelo - Chicago|Contour Airlines
        PHP 8,560PHP 26,120
        67% OFF
        67% OFF
        PHP 26,120PHP 8,560

        Choose Contour Airlines flights from Tupelo to Chicago. The one-way connecting flight with Contour Airlines departs from Tupelo Regional Airport on Tue, Feb 25, arriving at O'Hare International Airport. One-way Prices start from PHP 8,560 including taxes and charges.

      • TUP07:45 am
        23h 39m
        1 stop
        ORD07:24 am
        Mon, Mar 24|Tupelo - Chicago|Contour Airlines
        PHP 10,020PHP 26,120
        62% OFF
        62% OFF
        PHP 26,120PHP 10,020

        Choose Contour Airlines flights from Tupelo to Chicago. The one-way connecting flight with Contour Airlines departs from Tupelo Regional Airport on Mon, Mar 24, arriving at O'Hare International Airport. One-way Prices start from PHP 10,020 including taxes and charges.

      • TUP07:45 am
        26h 9m
        1 stop
        ORD09:54 am
        Fri, Mar 14|Tupelo - Chicago|Contour Airlines
        PHP 13,897PHP 26,120
        47% OFF
        47% OFF
        PHP 26,120PHP 13,897

        Choose Contour Airlines flights from Tupelo to Chicago. The one-way connecting flight with Contour Airlines departs from Tupelo Regional Airport on Fri, Mar 14, arriving at O'Hare International Airport. One-way Prices start from PHP 13,897 including taxes and charges.

      • TUP07:45 am
        26h 6m
        1 stop
        ORD09:51 am
        Fri, Apr 4|Tupelo - Chicago|Contour Airlines
        PHP 14,049
        PHP 14,049

        Choose Contour Airlines flights from Tupelo to Chicago. The one-way connecting flight with Contour Airlines departs from Tupelo Regional Airport on Fri, Apr 4, arriving at O'Hare International Airport. One-way Prices start from PHP 14,049 including taxes and charges.

      • TUP07:45 am
        6h 47m
        1 stop
        ORD02:32 pm
        Thu, Feb 27|Tupelo - Chicago|Contour Airlines
        PHP 21,970
        PHP 21,970

        Choose Contour Airlines flights from Tupelo to Chicago. The one-way connecting flight with Contour Airlines departs from Tupelo Regional Airport on Thu, Feb 27, arriving at O'Hare International Airport. One-way Prices start from PHP 21,970 including taxes and charges.

      • TUP07:45 am
        6h 47m
        1 stop
        ORD02:32 pm
        Mon, Feb 24|Tupelo - Chicago|Contour Airlines
        PHP 22,050
        PHP 22,050

        Choose Contour Airlines flights from Tupelo to Chicago. The one-way connecting flight with Contour Airlines departs from Tupelo Regional Airport on Mon, Feb 24, arriving at O'Hare International Airport. One-way Prices start from PHP 22,050 including taxes and charges.

      • TUP07:45 am
        26h 9m
        1 stop
        ORD09:54 am
        Sun, Mar 2|Tupelo - Chicago|Contour Airlines
        PHP 22,202
        PHP 22,202

        Choose Contour Airlines flights from Tupelo to Chicago. The one-way connecting flight with Contour Airlines departs from Tupelo Regional Airport on Sun, Mar 2, arriving at O'Hare International Airport. One-way Prices start from PHP 22,202 including taxes and charges.

      • TUP01:00 pm
        3h 5m
        Nonstop
        CHI02:00 pm
        Mon, Mar 3|Tupelo - Chicago|Contour Airlines
        Find More Flights
        Find More Flights

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Tupelo to Chicago Flight Time

Flight info.
Departure
Arrival
Weekly Schedule

  1. LF3007

    Contour Airlines

    01:15 pm

    TUP

    1.9h

    03:10 pm

    DFW

    SMTWTFS
    Search

  2. AA2881

    American Airlines

    09:35 pm

    DFW

    2.3h

    11:54 pm

    ORD

    SMTWTFS

  3. LF3007

    Contour Airlines

    01:15 pm

    TUP

    1.9h

    03:10 pm

    DFW

    SMTWTFS
    Search

  4. UA1436

    United Airlines

    05:50 pm

    DFW

    2.5h

    08:21 pm

    ORD

    SMTWTFS

  5. LF3001

    Contour Airlines

    07:45 am

    TUP

    1.1h

    08:50 am

    BNA

    SMTWTFS
    Search

  6. UA1113

    United Airlines

    07:34 am

    BNA

    2.0h

    09:32 am

    ORD

    SMTWTFS

  7. LF3001

    Contour Airlines

    07:45 am

    TUP

    1.1h

    08:50 am

    BNA

    SMTWTFS
    Search

  8. UA5741

    United Airlines

    06:04 am

    BNA

    2.0h

    08:05 am

    ORD

    SMTWTFS

  9. LF3001

    Contour Airlines

    07:45 am

    TUP

    1.1h

    08:50 am

    BNA

    SMTWTFS
    Search

  10. UA234

    United Airlines

    07:11 pm

    BNA

    2.3h

    10:29 pm

    EWR

    SMTWTFS

  11. UA2164

    United Airlines

    06:00 am

    EWR

    2.8h

    07:46 am

    ORD

    SMTWTFS

  12. LF3001

    Contour Airlines

    07:45 am

    TUP

    1.1h

    08:50 am

    BNA

    SMTWTFS
    Search

  13. AA6263

    American Airlines

    05:34 am

    BNA

    1.9h

    07:30 am

    ORD

    SMTWT-S

  14. LF3001

    Contour Airlines

    07:45 am

    TUP

    1.1h

    08:50 am

    BNA

    SMTWTFS
    Search

  15. UA396

    United Airlines

    04:57 pm

    BNA

    1.9h

    06:52 pm

    ORD

    SMTWTFS

  16. LF3001

    Contour Airlines

    07:45 am

    TUP

    1.1h

    08:50 am

    BNA

    SMTWTFS
    Search

  17. UA1616

    United Airlines

    12:38 pm

    BNA

    1.9h

    02:32 pm

    ORD

    SMTWTFS

  18. LF3001

    Contour Airlines

    07:45 am

    TUP

    1.1h

    08:50 am

    BNA

    SMTWTFS
    Search

  19. AA4001

    American Airlines

    10:21 am

    BNA

    1.7h

    12:02 pm

    ORD

    SMTWTFS
Find more flights and airlines

When is the cheapest time to fly from Tupelo to Chicago?

We monitor flight fares to help you find the best deals effortlessly

Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

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

    Airlines adjust prices for flights from Tupelo to Chicago 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.

  • How much do flights from Tupelo (TUP) to Chicago (CHI) cost?

    According to Trip.com's data, the lowest price is around PHP 18,228.

  • What is the transportation method from the main airport to downtown in Chicago?

    • The distance from O'Hare International Airport to downtown is about 25 km. It takes about 40 minutes by taxi.
    • The distance from Midway International Airport to downtown is about 14 km. It takes about 30 minutes by taxi.

How to find a cheap flight from Tupelo to Chicago

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Tupelo to Chicago. Book your flights at the right time and save more.
1
Book Early
Once prices are gone, they're gone. Lock in deals while you can!
2
Compare Flight Prices
Compare prices on travel agency and airline websites.
3
Look Out for Deals
Check airline and travel agency websites for latest flight deals
4
Check One-way Fares
Buying two cheap one-way flights can sometimes be a better deal than a round-trip.
5
Try Different Dates
Flying during the week, early in the morning, or late at night can help save money.
6
Use the Trip.com App
Save up to £10 per person when booking your flights on Trip.com

Flight Info | Tupelo to Chicago

Cheapest nonstop flight pricePHP 8,560
Off-season for travelFebruary
Peak season for travelNovember
Flight distance851.54 km
Popular airlineContour Airlines

Contact Us

About

Other Services

Payment Methods
Our Partners
Copyright © 2025 Trip.com Travel Singapore Pte. Ltd. All rights reserved
Site Operator: Trip.com Travel Singapore Pte. Ltd.