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All the Places You Can Visit from Chicago for Less Than $20

Cheap bus and train travel from Chicago.

It’s difficult to say goodbye to the extraordinary city that is Chicago, but if you’re looking for new places to explore, we found cheap bus and train tickets to 37 destinations that you can wander off to if you need a break from the Windy City.

For less than $20, you can travel to happening cities like Louisville, Cincinnati, and Milwaukee. As you can see below, you can even reach some of them for as low as $1.

Pressed for time but still need a getaway? Treat yourself to a day trip away from Chicago – there are plenty of fun local destinations you can check out without breaking the bank or using any of those precious vacation days.

If we didn’t list your dream destination, or if you feel like splurging on a more expensive trip, be sure to check out our Explore search tool to discover other places to visit out of Chicago based on your budget.


Route $1 Deals? Cheapest Avg. Price
Chicago to Coralville $20.00


Route $1 Deals? Cheapest Avg. Price
Chicago to Louisville $13.84


Route $1 Deals? Cheapest Avg. Price
Chicago to St. Louis $15.08


Route $1 Deals? Cheapest Avg. Price
Chicago to Cincinnati $19.03


Route $1 Deals? Cheapest Avg. Price
Chicago to Milwaukee $7.75

What is Cheapest Average Price?

The cheapest average price is the average amount of all of the cheapest bus or train prices available on Wanderu for a certain route over a 30-day period.

Bus and train carriers utilize what is known as dynamic pricing to determine ticket prices. That means that when a specific trip goes on sale (usually within four to six weeks prior to the trip date), tickets for that particular bus or train start at a certain low price and then get more expensive the more tickets are sold for that trip.

The cheapest average price may vary according to availability and carrier changes.

How to score the $1 deals

For certain routes, some bus carriers offer a starting ticket price of $1. That’s usually the price for the first couple of bookings for a bus that was just released for sale. Therefore, the earlier you book your trip, the higher chance you have of scoring a $1 deal.

However, if a bus sells out and the carrier decides to add another bus for the same date and time to meet the high demand, then the pricing cycle is reset, giving you the chance to score a $1 ticket at the last minute.

At Wanderu, we always bring you the best available deals out there and we’ve got even more tips to help you score really cheap bus tickets.

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About the author
Staffo Dobrev

Staffo Dobrev

Having lived in some of the greatest cities in the world, Staffo has always had a soft spot for travel and adventures. Instead of hitting the usual tourist attractions, though, Staffo prefers to make friends with local people and check out fun places and activities that are not in the travel books.

Come wander with us!

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