Weekend City Picks: Chicago

Buckle up, because Chicago’s list of bragging rights is a long one. Internationally renowned architecture, comedy, culture, cuisine, not to mention a lake that might as well be a freshwater ocean — it’s all here, waiting to be had. Add to that list a new elevated park on the Northwest Side and burgeoning development along the Chicago River, and this is a Second City with no shortage of first-rate attractions.
Weekend City Picks: Chicago

Arts & Entertainment

Art Gallery Tour

Art lovers will be drawn to the intersection of Superior and Franklin, the epicenter of River North’s upscale gallery district. Get a closer look at the paintings and sculptures on one of Chicago Gallery News’s free tours that take off at 11 a.m. Saturdays from the Starbucks at the corner of Franklin and Chicago. Get caffeinated because you’ll be visiting four galleries on the 90-minute excursion. 

SummerDance

SummerDance Chicago

Learn how to tango, waltz or samba and then put those free lessons to use at this popular summer event held weekends at Grant Park’s Spirit of Music Garden through Sept. 13. Live bands and DJs crank out the tunes while folks of all ages get down to the beat on the 4,900-square-foot open-air dance floor. 

Catch Some Comedy

Take in a performance at The Second City to see where Bill Murray, Tina Fey, Stephen Colbert — and just about everyone who’s funny — cut their comedic teeth. The legendary institution has multiple venues besides the Mainstage, so don’t be afraid to check out an obscure act — today’s unknown could be tomorrow’s big star. Want more? Head over to iO Theater’s impressive new digs at 10:30 p.m. Wednesdays when two of the city’s best improvisers, TJ Jagodowski and Dave Pasquesi, put on an hour-long impromptu play. 

Ravinia

Pack a picnic blanket, some food and wine (or stock up on the spot) at this gem of an outdoor concert venue in north suburban Highland Park. The summer home of the Chicago Symphony Orchestra caters to a wide range of musical tastes through mid-September. Some 3,400 seats populate the pavilion but the lawn is the way to go to soak up the true Ravinia experience. Even if you have a car, take the train: Metra’s Union Pacific North Line stops right outside the entry gate. You won’t have to worry about traffic or parking. Or having another glass of wine.

Food & Drink

Girl & The Goat

“Top Chef” winner Stephanie Izard is a true believer in farm-to-table cuisine. A good portion of the ingredients that go into her creative menu comes from local purveyors. The wood-oven roasted pig face tastes a lot better than it sounds, and you’ll be hard-pressed to find a place that serves goat in so many mouth-watering combos, from confit goat belly with bourbon butter, lobster, crab and fennel to goat empanadas with smoked blueberry tapenade. 

RPM Italian

RPM Italian Chicago

Celebrity couple Bill and Giuliana Rancic are part owners of this sexy establishment, but RPM has a lot more going for it than a pair of well-known proprietors. The real star here is the food. It would be easy to never make it beyond the menu’s appetizer section and fill up on the plump, moist meatballs, the truffle garlic bread and other savory treats. Rookie mistake. Save room for the homemade pasta and if you’re still hungry, dig into the 38-ounce prime, dry-aged Bistecca Fiorentina for $135 (serves two-to-four people). 

avec

The minimalist, all-wood décor makes this West Loop hot spot look like a Swedish sauna. And that’s about the size of chef Paul Kahan’s uber-popular eatery, where friends, couples and strangers cozy up to one another at the long communal tables to feast on delicious Mediterranean-inspired (mostly) small plates. The chorizo-stuffed Medjool dates have been a staple here for more than a decade. They’re a must. So is the focaccia, a humble dish elevated to new heights in this lively spot, which recently started serving lunch.

Milk & Honey Café

Grab a table on the sunny patio or snuggle up by the fireplace at this cozy Wicker Park café. It’s all about freshness and flavor at this bargain-priced breakfast and lunch joint, where ample sandwiches run around $8, as does the orange brioche French toast with toasted almonds and maple syrup. Grab a bag of the homemade milk and honey granola to go.

Family

Bobby’s Bike Hike

This easy, two-wheeled tour from Bobby’s Bike Hike is tailored to families with kids whose ages are in the single digits. You’ll log under five miles in the saddle, leaving plenty of time (and energy) to pet the animals at Lincoln Park Zoo, poke around a hidden garden and cruise along the stunning lakefront path. The guided tours are available Memorial Day through September and should be reserved at least a day in advance. 

Jazzin’ at the Shedd

Jazzin’ at the Shedd
 
Plan your visit on a Wednesday for an evening of music, cocktails and fireworks from the terrace of the famed aquarium, where the summer ritual known as Jazzin’ at the Shedd lasts from 5 p.m. to 10 p.m. (season ends Sept. 9). Whatever time you go, don’t miss the chance to touch a stingray before hopping over to a new special exhibit devoted to amphibians. 

Movies in the Parks

More than 240 films are screened outdoors at Chicago parks each summer. Plenty of kid-friendly options pack the schedule, making for a fun night of entertainment under the stars. Upcoming flicks in late August include “Annie” (Abbott Park), “Maleficent” (Rosenblum Park), “Rio 2” (La Vallita Park) and a Chicago classic, “Ferris Bueller’s Day Off” (Hiawatha Park).

Healthy Living

Workouts in the Park

Millennium Park’s Great Lawn turns into a giant al fresco gym Saturday mornings with exercise classes — tai chi, yoga, Pilates, Zumba — offered June through Labor Day weekend. The free, 45-minute workout sessions run from 7 a.m. to 11 a.m. During the week, start your Wednesday with a warrior pose at the 7:30 a.m. yoga class.

Soul Cycle

Pedal off that deep-dish pizza during an invigorating 45-minute class at this sleek indoor cycling studio. The New York City-based chain recently set up shop in Chicago with a couple of conveniently located outposts in Old Town and the Loop.

Kayak Chicago

Kayak Chicago
 
Hit the water and put that upper body to work on a kayak trip on Lake Michigan or the more sedate Chicago River. The outfitter Kayak Chicago rents one- and two-person vessels by the hour or day. The company also offers a slew of tours, including a six-mile round-trip river paddle on Wednesday and Saturday nights that culminates with fireworks at Navy Pier.

Outdoor 

Divvy Bikes

The ever-expanding network of sharable Divvy bicycles makes it easy to explore the city’s myriad neighborhoods and the lakefront path, an 18-mile ribbon of pavement hugging the Lake Michigan shoreline. Less than $10 gets you a 24-hour pass with access to Divvy’s inventory of nearly 5,000 blue three-speeds spread across Chicago. Keep each trip under a half hour to avoid overtime charges and download the free CycleFinder app to locate nearby bike-sharing stations.

Inside Chicago Walking Tours

Tour guide Hillary Marzec not only commands a deep knowledge of architecture, she’s trained in the homegrown art of improvisational comedy to boot. The result: fun, informative, nearly two-hour walking tours that put the city’s iconic buildings in perspective with stories about the people and events that helped shape the skyline. She leads a variety of outings Fridays through Mondays and can be booked for private excursions the rest of the week.

The 606

What was once an elevated rail line has been transformed into a linear park connecting the Northwest Side’s diverse neighborhoods of Humboldt Park, Logan Square, Wicker Park and Bucktown. A dozen access points along the 606 — named for the zip code prefix shared by all Chicagoans — lead up to a lofty, car-free oasis, where the newly completed 2.7-mile Bloomingdale Trail brims with joggers, cyclists and parents pushing strollers. 

Chicago Botanic Garden

Chicago Botanic Garden
 
Despite the name, the garden is actually located about 20 miles north of the city in suburban Glencoe. Don’t let that stop you from visiting these gorgeous 385 acres, open year-round and offering free admission. (No rental car? The garden is within walking distance from Metra’s Braeside train station on the Union Pacific North Line.) The Garden Chef Series teaches you how to turn farm-fresh ingredients into gourmet fare Saturday and Sunday afternoons through Oct. 4.

Shopping

Magnificent Mile

Magnificent Mile

Michigan Avenue’s eight-block stretch from Oak Street to the river is lined with enough retail to drain even the deepest of pockets. Tiffany, Cartier, Burberry and Saks rub elbows with The Gap, H&M and Express on the Mag Mile, where the old Water Tower and Pumping Station gives a glimpse of what this legendary boulevard used to look like before the Great Chicago Fire of 1871. If you have kids in tow, pop into Water Tower Place mall (835 N. Michigan) to visit the LEGO Store and the doll emporium that is American Girl Place, which also serves afternoon tea at 4 p.m. 

Merchandise Mart

Covering two city blocks and reaching 25 stories high, the Mart ranks as the world’s largest commercial building. The vast majority of its interior design-focused showrooms, however, are only open to those in the trades. The general public is invited to shop the first and second floors, with the former being home to 30-plus luxury kitchen and bath showrooms sure to get you in the home-renovation mood. Lots of fast food options — including Chicago’s addictive Garrett Popcorn — can be found on the second floor of this architectural behemoth. 

Trunk Club

This company works online with male customers and sends them trunks full of clothing, but it also has a few brick-and-mortar locations for those who want a more hands-on experience. At the club’s hip headquarters in River North, men can schedule a one-on-one appointment and try on a whole host of different looks. Kick back with a complimentary drink from the 40-foot bar while your personal stylist picks out your wardrobe. 

P.O.S.H.

You can spend a surprisingly long time in this quaint boutique perusing its flea-market finds, silver soup tureens and vintage tableware from historic hotels and cruise ships. Make no mistake: This is not some musty resale shop. The carefully curated inventory is a mix of old and new, with many of the “old” items never having been used. They’ve been sourced from unopened boxes in swanky establishments' storage rooms. This unique place is the perfect antidote to today’s mass-produced consumer culture. 
  

 

Hotels featured in this article

View all hotels in Chicago ›

You might also like

Close

Why book here?

When you book on spg.com, our hotel brand sites or SPG apps, you get more than a great room.

Best Rate Guarantee*

If you find a lower qualified rate** within 24 hours of booking, we’ll match it–and give you a 20% discount or 2,000 Starpoints®.

Earn Free Nights

Our sites and apps are the only places to earn Starpoints on hotel bookings.

Free In-Room Internet

Get free Internet when you book on spg.com, our hotel brand sites or SPG apps.

* The Best Rate Guarantee does not apply to taxes, gratuities, or any additional resort or guest charges or fees that may apply at SPG Hotels.
** Qualified rate means it satisfies all the Terms and Conditions of the BRG program including the required timeframe of receipt of the claim 24 or 48 hours prior to the standard check-in time.