Why You Should Visit Chicago

Located in the heart of the Midwest, Chicago is a beautiful, vibrant city with something to offer year-round. Between relaxing on the beaches of Lake Michigan in the summer, sampling the city’s renowned food offerings, or hanging out with friends at one of the city’s many famous bars or music venues, you’ll never be short on things to do in the Windy City.

Getting There

If you’re traveling from the Midwest, the best budget option will be a bus or train, arriving at Chicago’s Union Station. From there, you can ride the El (Elevated Train) to your final destination.

If you’re flying, you’ll land at either O’Hare or Midway airport. Chicago has great public transportation connecting its major airports with downtown, so hop on the Orange Line train from Midway or the Blue Line train from O’Hare and you’ll be in the city center in no time.

Where To Stay

 If you’re traveling solo or on a budget, hostels are a great option in terms of value for your money and a place to connect with other travelers. Here are a few that I’d recommend:

• Wrigley Hostel (Starting at $23/night)
• Urban Holiday Lofts (Starting at $16/night)
• HI Chicago (Starting at $29 / night)

Wrigley Hostel is located in the heart of Wrigleyville, steps away from Wrigley Field, home of the Chicago Cubs, and directly in the middle of one of Chicago’s best nightlife districts, but a little further away from the Loop and some of Chicago’s main attractions.

Urban Holiday Lofts is located in the Wicker Park / Bucktown area, a vibrant neighborhood filled with all the restaurants and bars you could imagine, and only a few train stops away from downtown.

HI Chicago is located in the Loop, just steps away from Grant Park and many of the city’s best attractions.

Keep in mind that Chicago hostel prices and availability can vary significantly, especially during the city’s numerous summer festival weekends, so be sure to plan early and budget accordingly. If hostels aren’t your thing, you can check AirBnB for similarly priced options or splurge on one of the city’s many beautiful hotel properties.

Chicago is absolutely beautiful in the summer, but if you’re looking for a more affordable getaway, aim to visit during shoulder season, in the spring or fall. I’d advise against visiting in January unless you particularly enjoy subzero temperatures and don’t mind not being able to go outside, but the city is wonderful year-round.

Chicago’s Must-See Destinations For The Budget-Conscious Traveler

Downtown

One of the first stops on any Chicago trip should be Millenium Park, where you can visit Cloud Gate (the Bean), one of Chicago’s most photographed attractions, and many other unique art installations and gardens.

Chicago is known for its astounding architecture, so just strolling around the Loop and the downtown area is a treat in itself. If it’s warm enough, be sure to check out the Riverwalk, which spans between Lake St. and Lake Shore Drive. The wide pedestrian walkway is lined with restaurants and green spaces to enjoy a picnic lunch down on the water.

For the history or architecture buffs, you can also take a free* walking tour or two to explore the downtown areas while learning about the history of the city and the significance of its landmarks. If you’re visiting in the spring or fall, don’t forget to bring a jacket, an umbrella, and a hot beverage to keep warm. (*Don’t forget to tip your tour guides!)

If the elements are too much, pop into the Chicago Cultural Center, right across the street from Millennium Park. This beautiful, historic building hosts hundreds of free events per year and is always free to visit.

If museums (or indoor activities) are your thing, consider investing in the CityPass for discounted admission to the Shedd Aquarium, the Field Museum, the Adler Planetarium, the Art Institute, and many other attractions throughout the city. They’re definitely worth a visit, but will each typically run you around $24 per person for entry, so keep that in mind when budgeting your trip. If that’s a bit above your price range, the city is home to dozens of smaller, free museums and attractions such as the Chicago Design Museum, the City Gallery at Water Tower Place, the Garfield Park Conservatory, the Jane Addams Hull House Museum, and many, many others.

Since Chicago is such a massive, sprawling city, one of the best ways to take it all in is from above. Skip the pricey ticket to the top of the Willis Tower and check out the views from the Signature Lounge on the 95th floor of the John Hancock Building, Chicago’s second tallest skyscraper. It’s free to go up if you’re heading to the bar, and you can take in the sights for just the cost of an overpriced cocktail while relaxing after a long day of window shopping on Michigan Avenue.

Beyond Downtown

If you’re visiting in the summer, keep an eye out for one of Chicago’s many festivals. These range from the well-known (read: more expensive) festivals such as Taste of Chicago or Lollapalooza to smaller neighborhood festivals. Downtown Chicago is beautiful and historic, but one of the best ways to experience the city is to venture out into one of the neighborhoods and get to know the locals. A quick Google search or chat with your hostel front desk staff will point you to some of these numerous, seriously underrated events.

For most of the year when the temperatures are bearable, Chicago is a beautiful city to visit, whether as a short weekend getaway from somewhere in the Midwest, or part of a bigger adventure.

Suggested next reading: Why Chicago Is (Perhaps) The Best City To Visit In The U.S.