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Osceola, IA, USA to Chicago, IL, USA from $15: 4 ways by bus, train, flight or car

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

How to Get from Osceola 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.

$15 by trainBest price
523 kmDistance
2h 59m Fastest

Compare Train, Bus, Flight, and Driving Options

Get detailed, step-by-step directions below for your trip from Osceola 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
Taxi
Plane
Average Duration
2h  59m
Estimated price
$137-413
Recommended
Company
Amtrak
Train
Average Duration
7h  10m
Estimated price
$15-140
Cheapest
route map
Distance: 523 km
Duration: 2h 59m

See more options

Company
Various
Drive
Average Duration
6h  20m
Estimated price
$65-100
Company
Various
Bus
Average Duration
8h  52m
Estimated price
$98-192

Traveling From Osceola to Chicago

Traveling from Osceola to Chicago offers a striking contrast between the serene charm of small-town life and the vibrant energy of a bustling city.

Best Neighbourhoods in Chicago

Chicago boasts diverse neighborhoods, each offering its own character and charm.

Lincoln Park
• Home to the Lincoln Park Zoo and several parks.
• Vibrant dining and shopping options along Armitage Avenue.
Wicker Park
• Renowned for its hip boutiques and music venues.
• A thriving arts scene with trendy galleries.
The Loop
• Heart of the city's business and financial district.
• Features iconic skyscrapers and cultural attractions.

Best Times To Visit Chicago's Attractions

Knowing the optimal times to visit Chicago's top spots can enhance your experience.

Millennium Park
Visit early mornings on weekdays to enjoy the tranquility and avoid tourist crowds.
Art Institute of Chicago
Weekday afternoons are ideal for a quieter visit, allowing a more relaxed exploration.
Navy Pier
Go during off-peak seasons, like spring or fall, to skip the summer crowds.

Chicago Weather: What to Expect Year-Round

Chicago experiences a continental climate with four distinct seasons, offering hot summers and cold winters. Understanding the weather patterns can help you choose the best time to visit, whether you want to enjoy outdoor festivals or explore indoor attractions.

Dining Recommendation in Chicago

Indulge in Chicago's iconic deep-dish pizza at Lou Malnati's, where the flaky crust, rich tomato sauce, and gooey cheese create an unforgettable flavor experience. This vibrant dining scene, complete with bustling pizzerias and a diverse array of local ingredients, presents a stark contrast to the homestyle comforts often found in Osceola.

Osceola - Chicago operators

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

Train Show train routes
Contact phone
+1 800-872-7245
Website
https://www.amtrak.com/home.html

Train from Osceola Amtrak Station to Chicago Union Station

Average Duration
7h 10m
Estimated price
$15-140
Bus
Contact phone
+1-858-800-8898
Website
jeffersonlines.com

Bus from Osceola, IA to Des Moines, IA

Average Duration
Estimated price
0-0
Contact phone
1(800) 992-4618
Website
burlingtontrailways.com

Bus from Des Moines, IA to Chicago, IL

Average Duration
Estimated price
$65-1371
Plane
Website
aa.com

Plane from Des Moines Airport to Chicago O'Hare Airport

Average Duration
1h 28m
Estimated price
$1373-1374
Website
united.com

Plane from Des Moines Airport to Chicago O'Hare Airport

Average Duration
1h 29m
Estimated price
$1373-1375
Website
delta.com

Plane from Des Moines Airport to Chicago O'Hare Airport

Average Duration
3h 48m
Estimated price
$1376-1377
Other Show other routes

Other from Osceola to Des Moines

Average Duration
46m
Estimated price
$100-1373

Other from Osceola to Chicago

Average Duration
6h 20m
Estimated price
$65-100

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

Traveling between Osceola 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.

Useful tips for train travellers
• On the Amtrak Cardinal service, passengers can enjoy onboard catering options that include a café car offering snacks, beverages, and prepared meals. Be sure to check the schedule for meal availability, as times may vary based on the length of your trip.
• Amtrak offers several seating options for your journey from Osceola to Chicago: Coach Class (Economy), Business Class, and First Class. Coach Class is cost-effective but provides comfortable seating. Business Class features more spacious seats and quieter carriages, while First Class offers premium seating and extra amenities. Check Amtrak’s website for the latest fares and availability.
• For your train journey, Amtrak is the primary operator. You can visit their website at amtrak.com for booking and schedules. Other potential operators include Metra, but their services are mostly for shorter distances. Useful links for your route can include local transport schedules in Chicago at the CTA website (transitchicago.com) and station maps at Amtrak's official site.

Frequently asked questions

Find out more about the route from Osceola to Chicago.

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The distance between Osceola and Chicago is approximately 200 miles by road. Traveling by car typically takes around 3 to 4 hours, depending on traffic and road conditions. If you choose to take a bus, the journey may take around 4 to 5 hours, while a train could take approximately 5 to 6 hours, not including any potential layovers. Air travel would be quicker but involves time for airport logistics, making it generally less convenient for such a short distance.
The most cost-effective and time-efficient option for traveling from Osceola to Chicago is typically by car, especially if you are traveling with others to share fuel costs. A bus service can also be a budget-friendly alternative, often providing competitive fares and direct routes. While flying may be the fastest way to reach Chicago, the added costs of airfare and airport logistics often make it less practical for this distance. Overall, driving or taking a bus strikes a good balance between cost and time efficiency.
Travel costs from Osceola to Chicago can vary based on the mode of transportation. For driving, expect to spend about $30 to $50 on gas, depending on your vehicle's fuel efficiency. Bus tickets typically range from $25 to $50, while train fares can vary significantly, often costing between $45 and $100 depending on the service and time of booking. If you choose to fly, round-trip tickets can range from $100 to $250, making it the most expensive option for this route.
You can travel from Osceola to Chicago without using public transportation by driving your own vehicle or arranging for a ride with a friend or family member. Alternatively, you could consider using a rideshare service, which would provide door-to-door transportation but at a higher cost. If you prefer a more comfortable journey, you could also book a private car service or hire a taxi for the trip. Depending on your chosen method, the travel time will typically be around 3 to 4 hours by car.
To travel from Osceola to Chicago without a car, you can look into rideshare options like Uber or Lyft, as these services may be available in your area. Another option is to hire a taxi or a private car service for a more direct ride, though it may be pricier. Alternatively, you could arrange for a private shuttle service if available, which can provide a convenient way to reach your destination. Lastly, as a creative option, consider reaching out to friends or family who might be traveling to Chicago and see if you can carpool with them.
There is no direct train service between Osceola and Chicago which means you would need to make at least one connection if traveling by train. However, there are bus services that may provide connections to Chicago, but they typically require transfers along the way. Additionally, while there is no major airport in Osceola, you can drive or take a shuttle to a nearby city with an airport for direct flights to Chicago. Overall, while direct options are limited, various connections can facilitate travel between the two locations.
There are no commercial airports in Osceola so you would need to travel to a nearby city, such as Des Moines, to catch a flight to Chicago. The actual flight time from Des Moines to Chicago is about 1 hour, but with travel to the airport and check-in time, the total travel duration could be around 3 to 4 hours. Ticket prices can vary significantly, but you can typically expect to pay between $200 and $400 for a one-way flight, depending on the time of booking and availability. Keep in mind that additional costs may arise from getting to and from the airports.
Near Chicago you have a wide variety of accommodation options to choose from, ranging from luxury hotels to budget-friendly motels. Popular neighborhoods like the Loop, River North, and Lincoln Park offer many hotels with easy access to attractions, dining, and public transportation. If you're looking for a unique experience, consider boutique hotels or charming bed-and-breakfasts in the surrounding suburbs. Additionally, vacation rentals like Airbnb can provide a more personalized stay for families or groups.