How to Spend 24 Hours in Chicago

Chicago skyline view from the Signature Lounge | © Adam James / Flickr
Chicago skyline view from the Signature Lounge | © Adam James / Flickr
Photo of Liz Behler
13 February 2017

Maybe you have a long layover, or maybe you planned a last-minute mini-vacation to the Windy City. While 24 hours may not seem like a long time, you can actually get a lot accomplished – if you plan it right. Here is our go-to guide to help you hit the ground running.

First Evening

Head straight from the airport to the James Hotel to check in, and then head down to David Burke’s Primehouse, the hotel restaurant, for dinner. Chicago is known for its steakhouses, and this one doesn’t disappoint. Savor one of the dry-aged prime cuts (aged on the premises in their Himalayan salt-tiled room) along with a specialty cocktail.

After steak, walk a few blocks north to the Hancock Tower. Bypass the observation deck’s long lines (and steep price) by taking an elevator to the 96th floor’s Signature Lounge. Take in one of the best views in the city here, all for the cost of a drink. After paying the tab, grab a cab to the Green Mill, one of the city’s most iconic jazz clubs, to hear some of the best local and international acts around.


Shake off a late night (and probable hangover) with breakfast at Beatrix. Order some coffee – then wrestle with what to order (we love the braised pot roast and egg sandwich). They also have a menu of fresh-squeezed juices, which are ideal for helping to undo some of the previous night’s damage. After breakfast, spend the morning strolling Michigan Avenue (also called the “Mag Mile”), a mile-long stretch of high-end shopping mixed with notable Chicago architecture (like the Tribune Tower, Wrigley Building, and Chicago Water Tower).

South end of the Mag Mile | © Hammerin Man/Flickr


If the weather is nice, a boat tour is a must. Wendella, located at the northwest corner where Michigan Avenue meets the river, sells tickets for both river and lake cruises. For the best of both worlds, hop on a 90-minute combination tour that travels down one branch of the Chicago River before heading out onto Lake Michigan. Definitely bring a camera (and sunscreen – the sun can be brutal out on the water). After getting back on land, head to Portillo’s, a Chicago institution that serves up some of the best Chicago-style hot dogs in town, as well as another lesser-known iconic Chicago dish, Italian Beef.

Second Evening

Wind down the whirlwind tour with a stop in hip Wicker Park. Stroll the streets checking out the bookstores and vintage boutiques before heading to Big Star for some of the best tacos in town. Grab a seat on the always-busy patio and order up some tacos al pastor before heading back to the airport.

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