Spend the day — or a weekend staycation — eating, drinking and playing in one of Chicago’s most action-packed and iconic neighborhoods. It will delight tourists, suburbanites and city dwellers alike!
With more than 25 hotels, dozens of upscale restaurants, streets teeming with boutiques and department stores, several famous skyscrapers and historic landmarks, as well as access to Lake Michigan and the Chicago River, there truly is never a dull moment in Streeterville. If you live in the city, this Near-North Side neighborhood is well worth an afternoon spent exploring, and if you’re coming in from the ‘burbs, why not make a weekend staycation out of it? Here are some of our favorite places to dine, drink, play and relax in Streeterville.
Where to Eat
Chow down on an ooey-gooey deep-dish pizza. It’s the perfect classic Chicago meal to savor in this quintessential Chicago neighborhood. 29 E. Ohio St., 312-321-1000
Enjoy traditional Italian cuisine (think: bruschetta with pesto and parmesan, gnocchi in vodka sauce, white fish with lemon and capers) in an upscale environment. Pair your meal with a robust bottle of red, and you’ve got the makings for a splendid evening in Streeterville. 201 E. Grand Ave., 312-410-9909
When it’s a big, juicy burger you’re craving, Ditka’s is the place to go. With several salads on the menu as well as lighter fare like chicken wraps and fish tacos, Ditka’s is a great lunch option. Plus, it’s conveniently located off the Mag Mile, so you can duck in to refuel halfway through your shopping spree. 100 E. Chestnut St., 312-587-8989
Located on the fifth floor of the 900 N. Michigan building, Frankie’s Scaloppine lures shoppers with the aroma of hot pizza fresh from the brick oven. Choose from pies topped with delicacies like truffle oil and oyster mushrooms or classics like sausage and green pepper. The menu also includes pastas, meat and fish prepared with fresh, seasonal ingredients. 900 N. Michigan Ave., 312-266-2500
If you opt to spend the weekend in Streeterville, don’t miss out on brunch at Yolk. This family-friendly eatery serves up omelets and scrambles with all kinds of fillings as well as sweet treats like Nutella crepes. 355 E. Ohio St., 312-822-9655
What to Do
Enjoy award-winning Shakespeare-inspired productions while supporting this trailblazing company that partners with Chicago Public Schools to improve literacy and brings free entertainment to Chicago’s parks all summer long. 800 E. Grand Ave., 312-595-5600
A true night on the town includes live entertainment. Take in a play at this unique and intimate venue located right on the Mag Mile. 175 E. Chestnut St., 312-977-1700
Sip a craft beer or a specialty cocktail like the Pear Prosecco (St. Germain, Absolut Pears and bitters with a strawberry or lemon twist) while you bowl. After you’ve worked up an appetite, nosh on ahi tuna poke, pan-roasted Brussels sprouts and other thoughtful cuisine you wouldn’t typically expect to find at a bowling alley. 322 E. Illinois St., 312-245-8331
The gorgeous Chicago skyline just never gets old — especially when you’re viewing it from the 94th floor of the John Hancock Center. Grab a cocktail from Architect’s Corner, the new bar and café on the 94th floor, and watch the sun set behind the city. Thrill seekers will want to experience TILT, an all-glass observation deck that extends out over the Mag Mile. 875 N. Michigan Ave., 888-875-8439
Take in envelope-pushing art in a variety of different media at this sleek urban museum. On tap this winter is an exhibit called “Riot Grrrls,” featuring eight female painters, and a thought-provoking photography exhibit called “Witness,” which explores the relationship between photographer and subject. 220 E. Chicago Ave., 312-280-2660
You could probably spend an entire day exploring the new- and-improved Navy Pier, but this waterfront playground is certainly worth a stop on your Streeterville adventure. Take a ride on the 200-foot Centennial Wheel (excellent photo opps!) and then relax with a craft cocktail at Tiny Tavern, an outpost of popular Lincoln Square restaurant and watering hole Tiny Lounge. Families won’t want to miss Winter WonderFest, a 170,000-square-foot extravaganza of rides, activities, slides, indoor ice-skating and holiday décor at the Pier from Dec. 3 to Jan. 8. 600 E. Grand Ave., 800-595-7437
One of Chicago’s most beautiful landmarks, the original water tower is a nice respite from the hustle and bustle of the Magnificent Mile. Marvel at the construction of the building (which was built between 1867 and 1869, and was one of the only structure to survive the Chicago Fire of 1871), and enjoy rotating art exhibits inside. 806 N. Michigan Ave.
A stylish bowling alley and so much more, Pinstripes has bocce, a scenic outdoor patio and a full menu of inspired dishes like a filet mignon trio with Gorgonzola and Parmesan or maple-glazed salmon. Located in the historic River East Arts Center, the Streeterville location of this local bowling chain boasts spectacular views of Chicago. 435 E. Illinois St., 312-527-3010
Captain Streeter Statue
Pay homage to the man who gave Streeterville its name with a quick stop at the statue depicting Captain Streeter. George Wellington “Cap” Streeter, as the story goes, claimed the land now known as Streeterville after his boat got stuck in a nearby Lake Michigan sandbar in 1886. We wish it were still that easy to score a piece of prime lakefront real estate! Corner of Grand Avenue and N. McClurg Court.
How to Relax
Immerse yourself in timeless Chicago elegance at this iconic hotel. The central location makes The Drake an ideal home base for exploring Streeterville, and amenities like afternoon tea at Palm Court are sure to make your stay memorable. If you’ve got kiddos in tow, book one of the spacious two-bathroom family rooms. 140 E. Walton Place, 312-787-2200
This sultry new bar is a fun place to hear live music. The nightly entertainment lineup includes jazz trios, funk bands and more. 404 N. State St., 312-646-0660
“Everything beauty under one roof” is the motto here. Stop in for a blowout and a manicure before your night on the town. 835 N. Michigan Ave., 312-335-7622
Relax with a massage — and so much more — at this full-service day spa. Book a facial, mani/pedi, mud wrap and sugar scrub along with your massage for a full day of beauty that will leave you feeling completely rejuvenated. 1163 N. State St., 312-202-0213
There’s a full menu of massage services available at this chain, including reflexology, trigger point therapy and prenatal massage. Add on aromatherapy or a sugar foot scrub to your treatment. 345 E. Ohio St., 312-222-0808
Whether you’re in the market for a new winter coat, luxe bedding or a bottle of your favorite perfume, Neiman Marcus is the perfect starting point for your Streeterville shopping spree. 737 N. Michigan Ave., 312-642-5900
A day of shopping on the Mag Mile wouldn’t be complete without a stroll through Macy’s. Stock up on basics for the whole family, and then stop for lunch at the adjoining upscale food court at Water Tower Place. 835 N. Michigan Ave., 312-335-7700
More from Make It Better: