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ShermansTravel experts rely on years of collective travel experience to bring you the best money-saving tips for your vacation. We take a discerning look at all the attraction passes, public transportation options, and other local bargains to make sure you get the most bang for your buck while traveling.

Chicago Money-Saving Tips

Download Groupons

Groupon kicked off the discount coupon trend in the Windy City, so many of the company's newest initiatives go through Beta testing here. Check the Chicago site a few weeks before traveling to take advantage of any newfangled savings programs.

Layer your wardrobe

Indian summer in October and November is not unheard of, but neither is an April blizzard; prepare yourself for the city’s schizophrenic weather system by packing layers.

Skip the rental car company

Chicago traffic is miserable, even on its best days. Comfortable shoes and a CTA (Chicago Transit Authority) pass are all you need in this pedestrian-friendly city.

Take your butt outside

Illinois finally became a smoke-free state on January 1, 2008. This means that cigarette smoking is now prohibited in public places, including restaurants, nightclubs, and bars.

Eat like a local

Saganaki (flaming cheese), the jibarito (skirt steak and cheese on crisp plantains), and Italian beef sandwiches were all invented here. Visit Greektown, Humboldt Park, and downtown, respectively, to sample these Windy City staples.

Become grid savvy

Chicago is easier to navigate than an excel spreadsheet, and street signs are numbered to help you get your bearings in relation to downtown. For example, if you're at 1600 N Wells St., it means you're 16 blocks north of the Loop. If you're at 800 W. Armitage Ave., it means you're 8 blocks west of the Loop, and so forth.

Hit the Beach

On a windy day, Lake Michigan's choppy waves, bright blue hue, and sandy shores resemble a rollicking sea. Take advantage of the waterfront, and set up camp at one of downtown's free beaches; Oak Street, North Avenue, and Ohio Street beaches are popular choices.

Celebrate Summer

Summertime is Chicago's peak tourism season, but it's also when free and cheap outdoor activities dominate the social scene. Celebrate the few warm weather months like the locals do at one of the neighborhood fests, many of which are free to enter and feature big-name performers.

Take the Train

Metered spots are hard to come by (not to mention expensive) and Chicago police generously dole out parking tickets. Opt to ride the ‘L’ or take the Metra, a local commuter rail, if near a station.

Ditch Downtown

Leave the Loop and head to Chicago’s more residential neighborhoods for good eats. Keep an eye out for BYOB spots, where you can save a bundle by sipping fine wine at supermarket prices.

Check out a Ticket

If you have friends or relatives in the Chicago area, ask if their local library belongs to the Macy's Museum Adventure Pass. The program lets residents “check out” free or discounted admission tickets to 17 museums.

Always Check the Calendar

Don’t forget to look at the calendars for the Chicago Public Library ( and Chicago Cultural Center ( for year-round free programs and attractions.

Art and Design

Check out the latest in modern design at the notable Archicenter ( which offers free gallery talks (Mon., Fri., Sat. 12:30pm). Almost all of Chi-town’s museums, including the famous Art Institute of Chicago (, offer free days (the first and second Wednesdays of the month). 

Chicago’s Animal Kingdom

Chicago is home to hundreds of species living in its zoos and animal parks. Take a stroll through the Lincoln Park Zoo, which is always free, and check on the Shedd Aquarium’s website ( for its listing of free admission days. 

Seek Out Local Guidance

Chicago Greeter, a branch of the Global Greeter Network, provides local-led free walking tours of one of the city’s many neighborhoods ( Register 7-10 business days ahead of your visit to schedule a tour.

Enjoy the Surroundings

Grant Park’s Buckingham Fountain, one of the largest fountains in the world, has free water and light shows on summer evenings. The nearby Navy Pier is ideal for a stroll, plus a few of its attractions, like the Smith Museum of Stained Glass Windows and live music on the Beer Garden stage (May-Oct.;, are free. 

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