Photo by Erin via

In Chicago, there is no shortage of activities to keep you busy no matter what time of year you choose to visit. Aside from the iconic parks, festivals, theaters, museums, and shopping, Chicago’s picturesque skyline reflected in the waters of Lake Michigan is a sight to see for every traveler to the Windy City. Despite the popular reputation of the city, budget travelers have no need to fret. Plan your trip with the following tips, and you can land some great deals that will have you on your way to Chicago in no time.

Photo by Mike Morrison via

Photo by Mike Morrison via

Plan Your Travel Dates Accordingly

Spring and fall are your best bet for the perfect combination of price and weather. Plan your visit to Chicago in April through May or September through October to avoid the summer crowds and bitter Chicago winters. However, if you’re up for braving the Chicago winters you’ll be sure to find the cheapest rates, but remember to bundle up.

The “L” is Your Friend

It is extremely easy to get around in Chicago with its efficient public transportation system, and it’s much cheaper than driving and paying for parking in the city. The “L,” short for elevated train, connects with the subway system so you will have no problem reaching just about any destination within the city. If you are flying into town, you can take the blue line from O’Hare Airport or the orange line from Midway Airport right into the heart of downtown Chicago.

Photo by Erin via

Photo by Erin via

See Chicago on the Cheap

There’s no need to pay for a fancy bus tour when visiting Chicago. The budget traveler can explore the Windy City with plenty of free and inexpensive attractions. Free walking tours from the Cultural Center offer a perfect historical background. If you are still in the mood for more walking, window shop down Michigan Avenue, take a stroll through Maggie Daley Park or Millennium Park, or venture over to Navy Pier for a classic tourist hotspot.

Score Low-Cost Accommodation Rates

For a great deal and excellent location, check out the eco-friendly HI-Chicago Hostel. Rates start at just $30 nightly, and it offers plenty of free amenities like Wi-Fi, breakfast, sheets, towels, and even guided tours of the city. Don’t get too caught up by all the appealing perks, because when you are in a city like Chicago you have every reason to go out exploring as much as possible. If luxury is a priority, indulge in one of the top hotels in Chicago at reasonable rates, like the Intercontinental Chicago Magnificent Mile hotel. With prices starting at $129 per night, you’ll be transported to a classic historical era with all the modern conveniences you may need. Step outside and you’ll be right in the center of all of Chicago’s best sights and attractions.

If you’ve been thinking about visiting Chicago, you no longer have a reason to hesitate. Start planning now to experience all that Chicago has to offer.

This post is a part of the #HipmunkCityLove Project.


  1. Another tip is to take a food tour. Not as a cheap as a free walking tour but you get a lot of good grub and get in some walking, too.

  2. I lived in Chicago for several years and one of the great things to do is the architectural tour via boat. It goes down the river and through the heart of the city. From this vantage you get to see things and understand the history in a different way. Very cool.

    • Definitely! It’s a very unique type of tour, especially considering the impact of the Chicago fire and the fact that you are on a boat for the tour 🙂 Perfect addition to the list!

  3. Love Chicago (maybe not now in the winter) … unreal food, cool skyscrapers!

  4. Chicago is one of the best places to visit. There is so much to explore that you might even find 15 days less. This city has the potential to leave you mesmerised.

  5. Chicago is a great place to visit! Definitely easy getting around with the public transportation system. Thanks for giving these tips!

  6. Loved this post! I visit Chicago often and I found this to be very helpful!

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