Bluebird
Tupelo, Mississippi

Private charter · MDW → TUP

Chicago to Tupelo

522 miles. One price for the whole airplane.

Photo: Fredlyfish4 · CC BY-SA 3.0

Price your flight from Chicago to Tupelo

Trip type
1

Times are local to each departure airport.

The trip

Chicago to Tupelo, door to door faster.

Trade about 11½ hours on the road for about a short flight in the air. Bluebird flies you direct from Chicago Midway International Airport in Chicago to Tupelo Regional Airport in Tupelo, 522 miles in a private jet with two pilots up front. Need a different size of aircraft? We'll source one sized for the trip. The price is for the whole aircraft, with every fee and tax shown before you book.

Distance
522 mi
Flight
—
Driving
11½ hours
Passengers
Up to 1
MDWChicagoTUPTupelo
MDW → TUP522 miles direct

Departing Chicago

Airports in Chicago

  • MDW

    Major airport

    Chicago Midway International Airport

    Chicago · KMDW

    From downtown
    9 mi
    Longest runway
    6,522 ft

  • ORD

    Major airport

    Chicago O'Hare International Airport

    Chicago · KORD

    From downtown
    16 mi
    Longest runway
    13,000 ft

  • PWK

    Commercial airport

    Chicago Executive Airport

    Chicago/Prospect Heights/Wheeling · KPWK

    From downtown
    21 mi
    Longest runway
    5,001 ft

  • GYY

    Commercial airport

    Gary/Chicago International Airport

    Gary · KGYY

    From downtown
    21 mi
    Longest runway
    8,859 ft

Arriving Tupelo

Airports in Tupelo

  • TUP

    Commercial airport

    Tupelo Regional Airport

    Tupelo · KTUP

    From downtown
    3 mi
    Longest runway
    7,150 ft

  • K8M1

    Regional airport

    Booneville-Baldwyn Airport

    Baldwyn

    From downtown
    23 mi
    Longest runway
    5,003 ft

When you land

Things to do in Tupelo

Tupelo is the commercial hub of northeast Mississippi and best known as the birthplace of Elvis Presley, whose two-room childhood home is now a museum. The city’s economy is unusually strong for its size: it is a center for upholstered furniture manufacturing, Toyota builds Corollas at a plant in nearby Blue Springs, and North Mississippi Medical Center is one of the largest rural hospitals in the country. The headquarters of the Natchez Trace Parkway is here, and Civil War battlefields at Tupelo and Brices Cross Roads recall the region’s history.

  1. 01

    Elvis Presley Birthplace

    The two-room house built by Elvis’s father in 1934 is the centerpiece of a park that includes a museum, the church where he first sang and a statue of Elvis at 13.

  2. 02

    Tupelo Hardware Company

    In this downtown store, Gladys Presley bought her son his first guitar in 1946, and it still sells hardware alongside Elvis memorabilia.

  3. 03

    Natchez Trace Parkway Visitor Center

    The headquarters of the 444-mile parkway offers exhibits on the history of the Trace, with nearby nature trails and access to the scenic drive.

  4. 04

    Brices Cross Roads National Battlefield Site

    North of Tupelo, this battlefield marks a June 1864 Confederate victory led by Nathan Bedford Forrest, with an interpretive center and walking trail.

  5. 05

    Tombigbee State Park

    Southeast of the city, this wooded state park offers a lake for fishing and paddling, hiking trails, cabins and campsites.

  6. 06

    Downtown Tupelo

    Fairpark and Main Street are home to restaurants, shops and the Tupelo Elvis Festival, held in June with concerts and an Elvis tribute artist competition.

Explore Tupelo charter

Questions

Chicago to Tupelo flights

How long is a private flight from Chicago to Tupelo?

About a short flight in a private jet, for 522 miles direct. Driving the same trip takes about 11½ hours.

Which airports do flights from Chicago to Tupelo use?

You can depart from Chicago Midway International Airport (MDW), Chicago O'Hare International Airport (ORD), or Chicago Executive Airport (PWK) and arrive at Tupelo Regional Airport (TUP) or Booneville-Baldwyn Airport (K8M1). Pick whichever is closest to where you're starting and where you're headed.

How much does a private charter from Chicago to Tupelo cost?

The price depends on the date, departure time, aircraft and where the airplane is positioned. Enter your trip above to see an instant price for the whole airplane, with every tax and fee included.

Can I book a round trip between Chicago and Tupelo?

Yes. Choose round trip when you search, and pick your return date and time. Flights from Tupelo back to Chicago are priced the same way.

Return flight

Tupelo to Chicago

More flights from Chicago

More flights to Tupelo

Explore Chicago private charter and Tupelo private charter, airports and things to do. Arriving at Tupelo Regional Airport (TUP).

Chicago to Tupelo, on your schedule

Choose your departure time and see a price for the whole aircraft. Bring up to 1 passengers for the same price.

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