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Travel Hacks for Chicago – Save Time, Money, and Explore the Good Stuff

Travel Hacks for Chicago - Save Time, Money, and Explore the Good Stuff

The Windy City is full of adventure. While it can be intimidating, these travel hacks for Chicago will save you time, money, and explore the good stuff. Navigate the city and hit up the real hot spots while keeping your cash.

Related: Chicago Trip Tips – Locals Advice For Exploring the Windy City


If you want those stunning views of the city without paying a fortune at the Willis Tower (known to every true Chicago native as the Sears Tower), visit the Hancock Building instead. Hit up the Signature Lounge for drinks at night. The view will be stunning and you won’t have to pay for the privilege, just the drinks.

Thalia Hall, The Vic, and Lincoln Hall are all great venues with a smaller crowd. They still book amazing artists and have a talent for finding upcoming stars.

Before visiting the museums, check out your desired attraction’s website. Usually, you’ll find discounts or special days when your visit will could be free. You might have to be flexible on your travel dates, but you’ll save a ton of cash.


Get off the Loop and step out of the trendy River North to explore the culture of Chi-Town. Wicker Park, Lincoln Park, Logan Square, Fulton Market are all amazing and safe places to explore.

Downtown may be the big draw for nightlife, but you’ll have a great time barhopping in Bucktown or Old Town and save money.

Related: Cheap Must-Try Eats, Drinks, and Entertainment In Chicago


Cell phone service is notoriously bad downtown. Make sure you download maps or memorize your paths before you venture off into the city.

Bikes are a great and affordable way to get around Chicago. Just make sure you don’t bike on the sidewalks.

If you’re not veteran driver in Chicago, which is known for fast movers and aggressive drivers, avoid the left lane.

Utilize handrails and straps on the bus. You may think you’ve got the balance to stand a ride on the L or the bus, but you will topple over.

The water taxi isn’t just for fun. It’s a great way to get unique views and make your way from Union Station or Ogilvie Station to Michigan Avenue on the cheap.

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