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Oshkosh to Chicago train

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Oshkosh - Chicago Train Timetable

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Trip Summary

You can pick from 4 daily train trips between Oshkosh and Chicago. The average train journey from Oshkosh to Chicago takes 4 hours and 41 minutes, but some Amtrak train trips are as short as 3 hours and 34 minutes.

Distance155 mi (250 km)
Fastest train3h 34m
Lowest price£32.92
Most frequent serviceAmtrak
Train lines1

Train Trip Reviews from Wanderu Customers

Overall score for trains from Oshkosh to Chicago

(Based on 6 ratings and reviews)

4.7

5.0

Wiily

10 March 2024- Visiting friends

Amtrak

Pros: N/A. Cons: N/A. Tips: N/A.

5.0

Janet

22 November 2023- Vacation

Amtrak

Pros: The traveling to Chicago was easy from Oshkosh Wi to Chicago! Cons: Instead of a bus to Milwaukee a train all the way would have been great!! Hopefully someday the trains will come back to our area!! Tips: Check out the trains! Much more room on a train!!

5.0

Janet

23 November 2022- Vacation

Amtrak

Pros: Exploring Chicago, the lights, shopping, great restaurants! Tips: Loved the train ride to Union Station!

3.0

Rosemary

26 July 2019- Vacation

Amtrak

Pros: The train from Milwaulkee to Chicago was fabulous. Cons: The bus trip from Oshkosh to Milwaulkee was slightly chaotic. Tips: Travel by train not bus.

What is the price of a train ticket from Oshkosh to Chicago?

The average price for a train ticket from Oshkosh to Chicago is £33.92, Compared to most train fares, this is an excellent price. By booking your trip at least 16 days in advance, you increase your chances of scoring even cheaper tickets. But if you wait until the day of your trip to book tickets, expect to pay £3.01 more.

Monthly average prices

£40£32£24£16£8MJJASONDJFMA
Ticket prices for the train from Oshkosh to Chicago stay pretty consistent throughout the year. You can expect to pay around £32 regardless of when you plan to travel.

Prices as travel date approaches

£40£32£24£16£83020100

Since ticket prices on this route stay pretty consistent, you don’t need to book way in advance. However, we recommend buying your train ticket to Chicago at least 48 hours before your scheduled departure to prevent any unpleasant surprises, like last-minute surges in price or sold-out tickets.

Which train should you take from Oshkosh to Chicago?

Amtrak is the one and only train line which connects Oshkosh to Chicago. However, there are 4 trains per day to choose from.

TrainDaily TripsAvg. TimeAvg. Price
Amtrak44h 41m£36.26

  • Amtrak is the largest passenger railroad service in America, offering daily intercity trains to hundreds of destinations across the contiguous United States, as well as several cities in Canada. Every Amtrak train comes equipped with comfortable seats with extra legroom, as well as several four-seat areas with tables in the middle. In addition, each car has a freshly cleaned restroom, free WiFi and power outlets at every seat. There are also snack bars where you can purchase drinks or food during your journey. On average, there are 4 Amtrak trains from Oshkosh to Chicago every day, as well as 4 trips on the weekends, with prices starting from £33.

Frequently Asked Questions

While the train is the main method of transportation from Oshkosh to Chicago, it will only take you part of the way there. Please note that part of your trip will be on a different vehicle, most commonly a bus or express shuttle.

The distance between Oshkosh and Chicago is approximately 155 miles, or 250 kilometers. The average train journey between these two cities takes 4 hours and 41 minutes, although the absolute fastest you could get there is 3 hours and 34 minutes.

Looking for ways to pass the time? Most trains are equipped with Wi-Fi, which means you can stream music, browse social media or get some work done during your ride. That said, in case your train has a spotty signal, or is among the few without Wi-Fi, we also recommend downloading TV shows and movies to your mobile device in advance of your trip. That way the ride will fly by whatever the Wi-Fi situation.

On a weekly basis, the greatest number of passengers tend to travel by trains from Oshkosh to Chicago on Tuesday. Tickets for Tuesday tend to also be the most expensive. For savvy travelers looking for cheaper priced tickets search for travel departing on Wednesday. Wednesday also tend to have less passengers which may make boarding faster and let you snag your perfect seat.

The earliest train departs Oshkosh at 06:00 while the last train of the day leaves at 15:00. To see all scheduled departure times, use the search function on this page to get the full schedule for your specific travel dates.

There are 4 scheduled trains on most days. Unfortunately, none of them are direct connections, so you will need to disembark from your original train and board a connecting train during your journey. Don't forget to bring your carry-on luggage when you switch trains. In some instances, you may also be responsible for transferring your own checked baggage.

You can also take a train for your return trip from Chicago to Oshkosh.

City Information

Chicago

Known for its innovative architecture, cultural contributions to jazz and house music, and of course that irresistible deep-dish pizza, the many sights and experiences in Chicago make it one of the best urban vacation destinations for millennials and a top destination in Illinois.

You can't beat the views of the city and Lake Michigan from the SkyDeck in the Willis Tower; at over 1,300 feet, this is the highest observation deck in the U.S. Snap that classic selfie with the Bean in Millennium Park, then wander the many museums in nearby Grant Park. Navy Pier is a popular tourist hotspot for its parks, restaurants, and attractions right on Lake Michigan, and baseball fans will find paradise in Wrigleyville, home to the Chicago Cubs' Wrigley Field and sports bars galore.

Chicago's enormous parks offer plentiful opportunities for outdoor activities in gorgeous urban settings. Many companies offer kayak rentals or boat tours on the Chicago River, with special tours running on Saint Patrick's Day, when the entire river is dyed green. When you’re ready to buy some souvenirs from your epic trip, hit the big brand stores on the Magnificent Mile, or shop local in neighborhoods like Andersonville and Wicker Park. And don't miss the chance to laugh until you cry at The Second City comedy theater, famous for launching the careers of comedians like Tina Fey and Stephen Colbert.

Chicago is one of the biggest transportation hubs in the Midwest, and provides easy access to nearby destinations ideal for day trips, as well as international travel from two airports. Thanks to plenty of bus and train stations throughout the city, getting to the Windy City is a breeze.

Station Information

Where is the train station in Oshkosh?

Main departure station: UoW Gruenhagen Conf Ctr - 208 Osceola St

There is one train station in Oshkosh.

All train stations in Oshkosh:

  • UoW Gruenhagen Conf Ctr - 208 Osceola St

Where is the train station in Chicago?

Chicago, IL - Union Station - CHIUST-0

Image credit: Jeramey Jannene

Link to image attribution

Main arrival station: Chicago (Union Station), Illinois

The historic Chicago Union Station is the United States' third busiest train station and a hub for 15 Amtrak train lines with destinations throughout the country. The station also serves bus carriers like Greyhound, Indian Trails and Jefferson Lines, and offers connections to Metra commuter lines. Union Station is also just a quick walk to the nearest Chicago L lines. The current station was built in 1925, to replace the original one dating back to 1881, and today wows visitors with its impressive facade, massive columns, and opulent Great Hall. Located right in downtown and adjacent to the Chicago Loop, Union Station is equipped with many services and amenities, including phone charging stations, shops, and various food and drink options.

Train stations in Chicago:

  • Chicago (Union Station), Illinois

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