The Ultimate 72-Hour Itinerary for a Weekend in Chicago

When it comes to vacation planning, it makes sense to cram as much fun into one weekend as humanly possible. Especially when travel plans have to be carefully selected these days, a whirlwind trip of hitting all the best spots just makes sense. With that in mind, we’ve put together a 72-hour itinerary for Chicago, the perfect place to visit for a long weekend. It's a surprisingly ideal destination for fall and winter, when the city's coziness kicks into high gear. Whether you’re more into live music, theater, or architecture, Chicago has something to offer, and we’ll show you how to get it. Read on for our ultimate 72-hour guide to Chi City:


Noon: Downtown exploration

Hit all the touristy must-see spots with an exploration of Chicago’s visitor-friendly downtown district, where you can pose under The Bean and go full Ferris Bueller at the Art Institute of Chicago. A leafy stroll through the picturesque Lurie Garden en route to the lakefront is another excellent way to take in the scenery, as is the view (with cold beverage in hand) from 13 floors above Michigan Avenue on the panoramic outdoor patio at Cindy’s Rooftop.

Lurie Garden | Photo by K M/Flickr

3 pm: Chicago Riverwalk

The Riverwalk is another must-visit spot. Make your way to the lakefront to take in the sweeping views, and check out the Chicago Architecture Foundation’s Chicago River Architecture Cruise. It checks all the boxes with knowledgeable (but not annoyingly so) narration of the downtown architecture and a breezy open-air deck, ideal for enjoying the crisp fall air while learning about the city's history. Further up the Riverwalk is City Winery, a cozy wine bar perfect for warming up. There's also the Bridgehouse Museum if you're searching for more Chicago history. If you happen to be in town on one of their bridge-raising days, it's worth a visit.

Photo by Alicia Fierro

6 pm: Three Dots and a Dash

Since no one ever had a bad time at a tiki bar, you’ll want to get the party started before dinner with a tropical cocktail (or two) at the reliably fun Three Dots and a Dash. A pirate-themed treasure chest packed with Champagne and overflowing with dense white fog? Consider it an appetizer.

8 pm: Thalia Hall

Looking for a cool indie music venue in a renovated 1892 opera house? Look no further than Thalia Hall, where you can rock out to Pitchfork-esque bands in a jaw-dropping historic theatre that comes with several additional perks. One of them being the on-site Dusek’s Tavern, where you can grab an excellent pre-show dinner of Slagel farm beef tartare, wood roasted Mt. Lassen trout, or a griddled double cheeseburger. As an added bonus, the venue also comes complete with its own downstairs booze emporium Punch House, where you can drink something called “Space Juice” in cool rec room-styled digs. (If you’re looking for more live events, you also might want to check out Capturing Chicago's Creative Spirit, a diverse round-up of dance of dance, theater, and other world-class shows.)

Photo by Mobilus In Mobili/Flickr

Midnight: Rossi’s Liquors

Got anything left in the tank? Might be time to close out the night at a local downtown dive like Rossi’s. Knock back some drinks, make a few new friends, and disappear without saying goodbye. 



10 am: Walk the 606

Since it’s Saturday morning, it’s time to leave your downtown bubble and head out into the neighborhoods to explore. One of the best ways to peep a nice cross-section of some of Chicago’s coolest hoods is to take an urban hike along Chicago’s 2.7-mile Bloomingdale Trail (aka The 606), a tree-lined greenway in the style of NYC’s High Line located along a former elevated railway line cutting through the neighborhoods of Wicker Park, Bucktown, Humboldt Park, and Logan Square. If you're going to do some leaf-peeping while in town, this is the spot.

Clayton Huack

Noon: Parson’s Chicken & Fish

A short walk from the 606 (exiting at Humboldt Boulevard) takes you to the classic Chicago paradise that is Parson’s Chicken & Fish, home of perhaps the best damn patio in all of the land. There’s also friendly games of ping-pong, Parson’s-branded beer from local brewing powerhouse Revolution, and the chicken is the real deal. Fried, grilled, whatever. Just put it in your face.

2 pm: Shopping in Bucktown

At this point, you’ll want a low-impact activity to nurse your belly. Walk around nearby Bucktown to do some shopping, where you'll find gift stores and boutiques on North Damen Ave. Just to the south is Wicker Park, with similar offerings like the always-hip Buffalo Exchange or the delightfully-named vintage store Kokorokoko.

6 pm: Pequod’s

While we’re checking off classic Chicago experiences, it would be somewhat criminal to leave Chicago without trying some deep-dish pizza. Yes, it is touristy. Yes, it’s something that actual Chicagoans pretty much only eat when out-of-towners are within eyesight. And yet, it’s magnificent nonetheless. One of the best spots in the city to get your grubby little fingers on this signature local dish is Lincoln Park’s low-key neighborhood hang Pequod’s, where the caramelized crust and thick amalgamation of dough and cheese will leave you too happy to get into yet another argument about whether or not deep dish is actually pizza. Probably.

Photo by Timothy M. Schmidt

8 pm: Second City

It’s now time to go for the trifecta of archetypal Chicago experiences with a visit to the legendary The Second City to see some live improv. No, this isn’t like that time your buddy dragged you to see his weird improv show in an empty elementary school gymnasium. This is actually funny. Like, really funny.

Courtesy of Old Towne Ale House

11 pm: Old Town Ale House

No trip to The Second City is complete without a post-show recap at Old Town Ale House, the legendary booze emporium located across the street from the comedy club that has attracted a wide range of eccentric celebrities over the years. Come for the stiff drinks and the always interesting cast of characters; stay for the nude paintings of famous folks created by the bar’s owner.


10 am: Jackson Park

Start your final day in the city with a pilgrimage to Jackson Park, one of the crown jewels of the Chicago Park District system that includes a golf course, a sculpture by Yoko Ono, and several beaches. Be sure to check out the Garden of The Phoenix in Jackson Park, where you'll find one of the best locations for a fall stroll. Just north of the park you’ll find Promontory Point, where you can stare out into the lake to gaze upon one of the finest views in the city. Afterwards, grab brunch at the nearby Ascione Bistro.

2 pm: Museum Of Science and Industry

Just south of Promontory Point is the Museum of Science and Industry, the largest science museum in America. It's the best place to see some hands-on exhibits and do some stargazing at the Giant Dome theater, a five-story wraparound dome that'll have you feeling like you're really flying through galaxies. Plus, they're always current with the rotating exhibits, like the ongoing (until October 24th) exploration of Marvel science

4 pm: Public art crawl

An investigation of Chicago’s booming murals scene is a must for any Instagram-friendly visit. First, make your way north to the historic Bronzeville neighborhood, where the culture continues at art hubs like the Bronzeville Artist Lofts and South Side Community Art Center. They're also home to a number of galleries, like Gallery Guichard and Blanc. Then, keep going north to the vibrant art-filled community of Pilsen, where you'll find plenty of picture-ready murals along 16th street.

6 pm: Maria’s Packaged Goods

Not only is Bridgeport home of the first-place White Sox’s Guaranteed Rate Field, it’s also a fun neighborhood full of interesting watering holes like Maria’s Packaged Goods, one of Chicago’s top beer bars/slashies (half bar, half liquor store — it’s a Chicago thing.) Pick up a bottle to smuggle back on the plane. While you're there, swing by Kimski for some Polish/Korean fusion.

Photo by Adrian Gaut

Where to Stay:

The Robey
Those aiming to stay in the neighborhoods would be wise to post up at The Robey, the hip 89-room boutique hotel perched in a historic building at the corner of Wicker Park’s bustling main intersection. In addition to cool loft-style rooms and a prime location about halfway between downtown and Wrigleyville, The Robey boasts two rooftop bars including the must-hit 13th floor Up Room and the pool-equipped Cabana Club.

Hotel EMC2
Those looking to stay closer to downtown can get a taste of science with all the creature comforts you’ve come to know and love in Chicago’s Streeterville neighborhood at the awesome yet underrated Hotel EMC2. In addition to stylish rooms with hardwood floors and chic brass accents just off the Magnificent Mile, its sophisticated restaurant the Albert punches well above its weight.

Sophy Hotel
If the South Side’s historic Hyde Park neighborhood is more your speed (and why wouldn’t it be?), the art-filled Sophy Hotel offers comfortable and charming boutique accommodations that cover all your essentials in style. As an added bonus, you are within easy walking distance to some of Hyde Park’s most crucial hangs including Virtue, Valois, and The Promontory.

Jay Gentile is an award-winning freelance journalist specializing in travel, food & drink, culture, events and entertainment stories. In addition to Thrillist, you can find his work in The Washington Post, The Guardian, CNN Travel, Chicago Tribune, Lonely Planet, VICE, Outside Magazine and more. Follow @thejaygentile