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Non-Touristy Things to Do in Chicago: A 3-Day Itinerary

BY: Editors | Feb 20, 2017

The Bean, Navy Pier, the Willis Tower Skydeck. Yes, there are plenty of things to do in Chicago, but real Chicagoans don't spend their weekends at any of the places just listed—unless it's at the behest of a friend from out of town, that is. More than 50 million tourists visit Chicago every year, and most of them stick to the same few attractions and neighborhoods. But if you want to experience the city like a true local, look no further. We spoke to some of our favorite Chicago businesses, who helped us devise this weekend itinerary filled with the best non-touristy Chicago activities.

Day 1

Taste the Greek Isles at Pegasus Restaurant & Taverna

130 S. Halsted St. | Greektown

There are plenty of Mediterranean restaurants in Chicago, but for really authentic gyros and kebabs, head to Greektown. One of the most popular stops in this small neighborhood is Pegasus Restaurant & Taverna, the winner of back-to-back Diners' Choice awards from OpenTable. Go upstairs to the rooftop deck, which features stunning views of the skyline, and energize yourself for a long weekend with a gooey appetizer of saganaki and some chargrilled souvlaki.

Unwind With a Massage and Cocktails at Versailles Massage & Bar

1329 S. Michigan Ave. | Near Southside

Book now: Spa services at Versailles Massage & Bar starting at $89

What's more relaxing than a nice massage? How about a nice massage paired with a stiff cocktail? Those are the dual specialties at Versailles, a posh spa decorated to look like its namesake French palace. Unwind with a Swedish massage enhanced with hot lava stones as you sip a French martini spiked with raspberry liqueur.

Shop for the Latest Fashions at AKIRA

845 N. Michigan Ave. | Downtown

Boutique shops abound in the city, especially in its bustling Downtown. Amid all the competition, AKIRA has built its own mini-empire, outfitting men and women in modern, on-trend apparel and accessories from brands such as Calvin Klein, Minkpink, Joa, and Adidas. With a diverse, always-updating collection, Akira has something to fit just about any style, from skater girl to runway vixen.

Forget Deep-Dish at Marie's Pizza & Liquors

4127 W. Lawrence Ave. | Albany Park

Buy now: Pizza and beer deals at Marie's Pizza & Liquors starting at $16.50

When thinking about Chicago, most outsiders automatically conjure images of deep-dish pizza. But true Chicagoans stick to the type of thin-crust pie found at Marie's Pizza & Liquors. This old-school haunt has been serving ultrathin pizzas since 1940, and not much has changed about the restaurant's retro ambience since. And because Marie's features an adjoining liquor store, there's never a shortage of ice-cold beer to pair with your slice.

Day 2

Devour a TV-Lauded Lunch at BIG & little's

1034 W. Belmont Ave. | River North

Buy now: $12.50 for $20 worth of gourmet fast food at BIG & little's

Few Chicago restaurants have a menu as eclectic as the one at BIG & little's, the culinary brainchild of Gary Strauss ("Big") and Tony D'Alessandro ("Little"). Since opening, their restaurants have been featured in just about every local media outlet, as well as nationally on Diners, Drive-Ins and Dives and Mystery Diners. The hullabaloo is well-deserved, too, with long lines forming every day to get a taste of their softshell crab po'boys, poke tacos, and beer-battered burgers.

Get a New Look at Studio Within

3000 N. Sheffield Ave. | Lakeview

Book now: Salon and spa services at Studio Within starting at $15

It seems like just about every city block has a salon in Chicago, especially in uber-trendy Lakeview. But locals who want something a little funkier head to Studio Within, an eco-friendly salon with a quirky, vintage vibe. Stylists here specialize in all sorts of looks, from beachy waves and ombre highlights to retro pin curls and bobs.

Explore Exotic Spices at The Spice House

1512 N. Wells St. | Old Town

Surrounded by the neighborhood charm of Old Town, The Spice House beckons in foodies with its massive collection of spices and cooking accoutrements. Sample far-flung flavorings like African berbere or Peruvian aji chiles, or stock up on bulk spices for DIY baking and pickling projects.

Enjoy a Farm Dinner in the City at Bread & Wine

3732 W. Irving Park Rd. | Irving Park

This Michelin-recommended American brasserie serves up comforting, farm-to-table cuisine in a rustic atmosphere. Local ingredients shine in seasonal dishes such as Meyer Ranch rib eye with blue-cheese butter or shrimp-and-chickpea stew with saffron aioli. Be sure to sample one of the wines from the restaurant's private label while you're there, too. And keep your eyes peeled for Mayor Rahm Emanuel, who touts this as one of his favorite restaurants.

Pro Tip: Bread & Wine co-owner Lisa Fosler Kelly calls local brewer Half Acre "the best beer on the scene right now."

Day 3

Squeeze in an Early Workout at Moksha Yoga Center

2528 W. Armitage Ave. | Logan Square

Buy now: Yoga classes at Moksha Yoga Center starting at $29

After being featured in Shape magazine and the Chicago Tribune, Moksha Yoga Center quickly became one of the trendiest yoga studios in one of the city's trendiest 'hoods: Logan Square. Start your morning off right with a Mindful Flow or Ashtanga class, then spend a few minutes browsing the boutique stocked with eco-friendly and sustainable yoga accessories.

Eat Candy for Breakfast at Whisk

2018 W. Chicago Ave. | Ukrainian Village

Claim now: 30% cash-back at Whisk

When it comes to things to do in Chicago, Sunday brunch should be at the top of your list (because it's definitelyat the top of every local's). Though Whisk opened recently, it's already had to open a second location to house all the spillover crowds. Place your order—the chilaquiles and Snickers–stuffed french toast are local faves—and ogle all the dining room's whimsical artwork, including numerous portraits of the owners' muse: Ron Swanson from Parks and Recreation.

Feel Like a Kid Again at WhirlyBall

1825 W. Webster Ave. | Bucktown

WhirlyBall combines lacrosse, basketball, and bumper cars into one uniquely Chicago sport. Grab three friends (there's a four-person minimum to play), order up one of the 32 beers on draft, and prepare for one of the most competitive—and strangest—attractions in Chicago. If WhirlyBall itself doesn't trip your trigger, the facility also offers laser tag and bowling.

Extinguish Hunger at Tacos Tequilas

2919 N. Milwaukee Ave. | Avondale

Buy now: Mexican meals at Tacos Tequilas starting at $24 for two

In 2014, Chicago magazine's "Cheap Eats" issue called these tacos the best in the city. And for a place that's home to some of the finest Mexican food in the country, that's saying something. Start with an appetizer of flaming panela cheese, before moving on to some oh-so-tender cochinita pibil or lengua tacos, and make sure to save room for a slice of tres leches cake.