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Tupelo, MS, USA to Chicago, IL, USA from $60: 9 ways by bus, train, flight or car

Compare Travel Options and Prices

from
Tupelo, United States of America
to
Chicago, United States of America

How to Get from Tupelo to Chicago: Cheapest, Fastest and Best Way

1Map provides directions to cities, towns, landmarks, attractions, and addresses worldwide, offering thousands of multi-modal routes to easily get you from point A to point B.

$60 - Bus, TrainBest price
858 kmDistance
4h 50m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Tupelo to Chicago with 1Map travel planner. Easily compare ticket prices, explore various transport options, and find the best routes for a seamless and cost-effective travel experience.

Company
various
Drive
Plane
Average Duration
5h  28m
Estimated price
$71-360
Recommended
Company
Greyhound, Amtrak
Bus
Train
Average Duration
13h  41m
Estimated price
$60-267
Cheapest
route map
Distance: 858 km
Duration: 4h 50m

See more options

Company
various
Bus
Plane
Average Duration
6h  55m
Estimated price
$93-710
Company
various
Plane
Average Duration
5h  38m
Estimated price
$163-358
Company
various
Bus
Plane
Average Duration
6h  23m
Estimated price
$213-491
Company
various
Bus
Plane
Average Duration
7h  23m
Estimated price
$711-712
Company
various
Plane
Average Duration
4h  50m
Estimated price
$713-714
Company
Greyhound
Bus
Bus
Average Duration
17h  29m
Estimated price
$715-716
Company
various
Drive
Average Duration
10h  29m
Estimated price
$717-718
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Traveling From Tupelo to Chicago

The journey from Tupelo to Chicago spans a landscape rich in contrast, where the small-town charm of Tupelo transforms into the bustling urban life of Chicago, offering you a chance to experience serene backroads before diving into vibrant city energy.

Best Neighbourhoods in Chicago

Chicago's neighborhoods each offer distinct vibes and attractions for every traveler.

Wicker Park
• Renowned for its trendy shops and boutiques.
• A hub for live music and artistic events.
The Loop
• Features iconic skyscrapers and architecture.
• Home to major theaters and cultural attractions.
Lincoln Park
• Offers beautiful parks and lakefront views.
• Great dining options and vibrant nightlife.

Best Times To Visit Chicago's Attractions

Timing your visits can greatly enhance your Chicago experience.

Millennium Park
Visit early mornings on weekdays to enjoy the serenity and avoid crowds.
Art Institute of Chicago
Mid-afternoons are ideal, especially during off-peak seasons, for a calmer experience.
Navy Pier
Plan your visit during weekdays in the late morning for fewer tourists.

Chicago Weather: What to Expect Year-Round

Chicago experiences a varied climate with cold winters and warm summers, making spring and fall the most pleasant times to visit. Weather can significantly shape your travel plans, whether it's enjoying outdoor festivals in the summer or cozying up in museums during the winter.

Dining in Chicago: A Culinary Adventure

Try the acclaimed deep-dish pizza at Lou Malnati's, where the hearty, buttery crust and rich layers of cheese and toppings create a flavor profile that's a world away from Tupelo's Southern comfort food. The lively atmosphere in Chicago's pizza joints, combined with the use of local ingredients, offers a distinct dining experience that showcases the city's vibrant culinary scene.

Tupelo - Chicago operators

Explore transport companies operating between Tupelo and Chicago, with prices starting at . These companies offer competitive pricing, flexible schedules, and comfortable travel experiences.

Plane

Plane from Tupelo (TUP) to Chicago O'Hare (ORD)

Average Duration
2h 4m
Estimated price
$3605-3606

Plane from Huntsville (HSV) to Chicago O'Hare (ORD)

Average Duration
5h 28m
Estimated price
$71-360
Website
southwest.com

Plane from Tupelo (TUP) to Chicago Midway (MDW)

Average Duration
5h 38m
Estimated price
$163-358

Plane from Huntsville (HSV) to Chicago O'Hare (ORD)

Average Duration
5h 28m
Estimated price
$3604-360
Train
Contact phone
+1 800-872-7245
Website
amtrak.com

Train from Memphis to Chicago Union Station

Average Duration
10h 35m
Estimated price
$2678-601
Bus
Contact phone
+1 214-849-8100
Website
greyhound.com

Bus from Tupelo to Memphis Bus Station

Average Duration
1h 50m
Estimated price
$1635-607

Bus from Memphis Bus Station to Chicago Bus Station

Average Duration
14h 35m
Estimated price
$2670-3602

Bus from Tupelo to Birmingham

Average Duration
2h 40m
Estimated price
$1636-609

Bus from Tupelo to Memphis Bus Station

Average Duration
1h 50m
Estimated price
$1635-607

Tupelo to Chicago: Overview of Bus, Train, Flight, and Car Trips

Traveling between Tupelo and Chicago offers a variety of convenient options to suit your preferences, schedule, and budget. Whether you prioritize affordability, speed, or comfort, you’re sure to find the perfect way to travel without compromising on quality or convenience.

🚗 Starting your road trip from Tupelo to Chicago you'll embark on a scenic journey spanning 639 miles. Be prepared for roughly 10 hours and 29 minutes of driving time ahead. 🛣️ Along the route, you'll witness the changing landscapes from Mississippi to Illinois. The prices for this road trip adventure typically range between $110 to $170, providing flexibility for budget-conscious travelers.
Average price
$110 - $170
🛫 Flying from Tupelo to Chicago is a convenient and time-saving travel option. The direct flight from Huntsville Airport to Chicago O'Hare Airport takes just 2 hours and 4 minutes. 🛬 United Airlines, American Airlines, and Delta are the main carriers offering flights between Huntsville Airport and Chicago O'Hare Airport. The total travel time from Tupelo to Chicago by plane is approximately 5 hours and 38 minutes. 💸 Flight prices between Chicago and Tupelo can range from $163 to $358, making it relatively affordable to explore these two vibrant cities by air. Whether it's for business or leisure, flying is a quick and efficient way to reach the Windy City from Mississippi.
Departure Point
Huntsville Airport
Arrival Point
Chicago O'Hare Airport
🚌 Embark on a scenic bus journey from Tupelo to Chicago which takes approximately 17 hours and 29 minutes. Sit back, relax, and enjoy the changing landscapes as you travel through multiple states. 🎟️ Ticket prices for buses between Chicago and Tupelo can range from $90 to $205, offering budget-friendly options for travelers. Pack some snacks and entertainment for the ride, and get ready for a comfortable and affordable travel experience.

Frequently asked questions

Find out more about the route from Tupelo to Chicago.

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The distance between Tupelo and Chicago is approximately 533 miles, or 639 miles by road. The typical travel time by plane from Tupelo to Chicago is around 4 hours and 34 minutes. If driving, it would take approximately 10 hours and 29 minutes to travel from Chicago to Tupelo. Alternatively, taking a bus from Tupelo to Chicago would typically take around 12 hours and 24 minutes.
The most cost-effective and time-efficient transportation option for traveling from Tupelo to Chicago is by flying. It takes approximately 4 hours and 34 minutes to reach Chicago from Tupelo by plane and can cost between $110 and $380. Alternatively, taking a bus and train combination is a cheaper option, costing between $55 and $270, but it takes longer, with a travel time of approximately 13 hours and 41 minutes. Overall, flying is the quickest and most convenient option for this journey.
The prices for bus tickets between Tupelo and Chicago range from $60 to $195. The exact price will depend on factors such as the time of year, the specific bus company, and any promotions or discounts that may be available. It is recommended to check with different bus companies or online platforms to compare prices and find the best deal for your travel needs.
To get from Tupelo to Chicago without using public transportation, you can drive the 639-mile distance. The journey takes approximately 10 hours and 29 minutes by car. Depending on factors such as fuel efficiency and toll charges, the cost of the drive can range from $110 to $170.
If you don't have a car, the best way to travel from Tupelo to Chicago is by bus. The bus journey takes approximately 12 hours and 24 minutes and costs between $55 and $200. This option allows you to relax and enjoy the scenery along the way without the hassle of driving or navigating airports.
The flight duration from Huntsville Airport to Chicago O'Hare Airport is typically 2 hours. The prices of flights between Chicago and Tupelo can range from $113 to $378. It is important to note that these prices can vary depending on factors such as the airline, the time of year, and the availability of tickets.
There are plenty of options for accommodation near Chicago. With over 1116 hotels available, travelers can find a range of options to suit their preferences and budgets. Prices start at $58, making it possible to find affordable accommodation in the city. Travelers can choose from luxury hotels, boutique accommodations, budget-friendly options, and more, ensuring a comfortable stay during their visit to Chicago.

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