Sometimes, the best city to visit is your own. You get to look at your hometown with fresh eyes AND you have all the insider intel to tour it like a pro. From the skyscrapers to the comedy scene, this is how we do Chicago better than the tourists.

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the signature lounge cocktails chicago tourist attractions
Scott Thompson

Instead of Willis Tower Skydeck: Cocktails at The Signature Lounge

Yes, Willis Tower goes ten stories higher than the Hancock, but the latter's got the edge in terms of wait time. Skip the lines and grab a cocktail at The Signature Lounge on the Hancock’s 95th floor. Along with your time, you’ll save yourself some money. (Skydeck admission is $23; a drink at The Signature Room runs $10 to $15.) And definitely excuse yourself to powder your nose, because the view from the women’s bathroom is one of the best in the city.

tj and dave at io chicago tourist attractions

Instead of Second City: TJ & Dave at iO

Shoot west of Second City on North Avenue and continue on to iO (formally Improv Olympic). It’s here that T.J. Jagodowski (that guy from those hilarious Sonic commercials) and Dave Pasquesi (basically a Chicago theater icon) perform their long-running, entirely improvised show every Wednesday night. For an hour, they roll deep into a variety of characters, plots and subplots, which all interconnect in wild and hilarious ways. You will be awestruck. Guaranteed.

chicago water taxi tourist attractions

Instead of Chicago Architecture Tour: Chicago Water Taxi


Save money, skip the crowds and see a piece of the Chicago River we bet you haven’t. How? Take the Water Taxi from downtown to Chinatown. You’ll disembark at Ping Tom Memorial Park, where dim sum at Ming Hin and sesame bubble tea from Joy Yee’s await. If you’re really dying to know all the lore behind Marina Towers, download an audio tour here.

the bean at night chicago tourist attractions
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Instead of The Bean: The Bean at Night (Yep)

OK, Cloud Gate is actually pretty cool. But good luck trying to get a photobomb-free shot of it during the day. Come back after sunset, when the crowds are smaller and the city lights bounce off it in some pretty amazing ways. While you’re out there, wander south to Michigan and Roosevelt for a shot of Agora, a staggering assembly of 106 headless iron figures.

neighborhood fireworks navy pier chicago tourist attractions

Instead of Navy Pier Fireworks: Neighborhood Fireworks

Shhhh, you can actually see Navy Pier’s free Wednesday and Saturday night fireworks even better from Montrose Beach up north. Grab your crew and a picnic. On the Fourth of July, you’d be remiss to skip the massive displays put on by residents around Winnemac Park in Ravenswood.

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