The big surprise about Chicago is how much waterfront it has. On foot or on a rented bike, the 18-mile Lakefront Trail is the best way to experience the beaches, parks, and sites like Soldier Field and Navy Pier along Lake Michigan.
Lake Michigan & Congress Pkwy.
Chicago, IL
+1-312-747-2001
When your alumni roster includes Steve Carrell, Stephen Colbert, Mike Meyers, and Tina Fey – the new kids compared to John Belushi and Dan Aykroyd -- you can call yourself the world’s best comedy club. Sketch and improv with heavy audience participation are the focus of the daily performances.
1616 N. Wells St.
Chicago, IL 60614
+1-312-337-3992
This is a city rightly famous for its magnificent buildings. The most interesting way to see them and learn their history is on a Chicago Architecture Foundation river cruise. Offered daily from Spring through Fall.
224 S. Michigan Ave.
Chicago, IL 60604
+1-312-922-3432
A massive outdoor architectural wonderland next door to the Art Institute that draws everyone for the Crown Fountain’s video images of locals, concerts at the Frank Gehry-designed Jay Pritzker Pavillion, and Anish Kapoor’s massive bean-like sculpture Cloud Gate.
201 E. Randolph St.
Chicago, IL 60602
+1-312-742-1168
The cinema affiliated with the School of the Art Institute of Chicago is the city’s premier showcase for the best indie, international, and classical film. Programs include annual film festivals, lectures, and multimedia exhibitions.
164 N. State St.
Chicago, IL 60601
+1-312-846-2800
Chicago is rich with museums, but the Art Institute is a favorite for its little-known and wildly popular masterpieces, remarkable photography exhibits, and the gorgeous new modern wing. The museum shop is terrific, and gorgeous Terzo Piano restaurant on the rooftop has Millenium Park views.
111 S. Michigan Ave.
Chicago, IL 60603
+1-312-443-3600
The hot dog spot is always buzzing, partly due to all the hungry DePaul kids streaming in from across the street, but also because the impressive list of dogs are a city staple. But the "frips," a.k.a. fried potato chips, steal the show.
816 W. Fullerton Ave.
Chicago, IL 60614
+1-773-248-3647
The best dim sum in Chicago has been tapped by UChicago crowd. All the usual suspects are done well: the shumai, cha siu bao, and egg tarts never disappoint. For somehting special, get the Macau-style crispy pork belly.
2168 S. Archer Ave.
Chicago, IL 60616
+1-312-808-1999
Sharing the space with the popular Maria's Packaged Goods & Community Bar, Korean and Polish food come together deliciously at the counter-only spot. Go for the Ko-Po beef or the veggie potskis with kapusta filling.
954-960 W. 31st St.
Chicago, IL 60608
+1-773-823-7336
The tiny counter joint with the cutest interiors — ever-ready for that Instagram close-up — serves hearty bagels, cured fish, and breakfast tea.
2819 N. Southport Ave.
Chicago, IL 60657
+1-312-508-3286
Forget the three-hour evening/weekend wait times and try for an early weekday lunch. The double cheeseburger was named America's best, and the hardworking bartenders keep you occupied while you wait.
800 W. Randolph St.
Chicago, IL 60607
All of restuarateur Brendan Sodikoff's favorite things are in one large space: Small Cheval budgers, Dillman's pastrami, Doughnut Vault pastries. You could spend all day in the comfy, oversized leather couches or at the ping pong tables.
354 W. Hubbard St.
Chicago, IL 60654
+1-312-888-9195
Down a tiny alley just off crowded Randolph Row is a painted handprint on a non-descript door. Follow the steps down for the spiciest ramen in town. The daring should order the kanabo spice tonkotsu (and maybe a cocktail slushie to help numb the pain).
112 N. Green St.
Chicago, IL 60607
+1-312-754-0431
Waits are heavy, and with good reason: the food is incredible, though not for the faint-bellied. Standouts include pork-fried almonds, salt-roasted beets with whipped goat cheese, crispy pig's ear, and pork sweetbreads a la plancha.
500 N. Michigan Ave.
Chicago, IL 60611
+1-312-464-1744
The restaurant responsible for bringing farm-to-table to Chicago. After a recent renovation, the space retains its homey vibe and the food has been taken up several notches — and it was great to begin with. The menu changes daily and emphasizes seasonal and local. Brunch is equally exceptional, especially breakfast burrito and semolina griddle cakes.
2537 N. Kedzie Blvd.
Chicago, IL 60647
+1-773-489-9554
Save dessert for the morning. Specifically, cherry scones and sugar cream pie. Grab a window seat (there are only three tables), order a Metropolis coffee and your pastry of choice, and savor the goodness of pure butter and farm-fresh produce.
1618 1/2 Chicago Ave.
Chicago, IL 60622
+1-312-243-4846
A dimly-lit, Parisian-style haunt woos you with cocktails, then wins you over with velvety steak tartare, platters piled with fresh oysters and shrimp cocktail, mussels, rich cassoulet, and the best crème brulee you'll ever eat.
840 W. Randolph St.
Chicago, IL 60622
+1-312-243-9712
Chef Paul Kahan’s West Loop runs the gamut from The Publican, a loud, meat-heavy, beer-hawking brasserie, to Publican Quality Meats, the Jewish deli dreams are made of, with sandwiches as big as your head and a full grocery stocked with chefs' picks, to Avec, the tiny, wooden, small-plates restaurant that serves chorizo-stuffed dates, light-as-air brandade, taleggio flatbread, and wines from around the world.
837 W. Fulton Market
Chicago, IL 60607
+1-312-733-9555
You've heard of it because chef Stephanie Izard won "Top Chef." It's jam-packed with adventurous food-lovers who want to make dinner a destination. It's impossible to get in, but worth making a reservation months in advance. Alternatively, drop by the more laidback Little Goat Diner across the street.
809 W. Randolph St.
Chicago, IL 60607
+1-312-492-6262
The home restaurant of powerhouse American chef and molecular cuisine pioneer Grant Achatz, the man who made edible printer paper famous and survived tongue cancer. Every dish he serves is a meditation, a thought-provoking “how’d they do this” experience. In other words, a meal of a lifetime. If you want to try the $210 and $265 tasting menus, you'll have to get a ticket.
1723 N. Halsted
Chicago, IL 60614
+1-312-867-0110
Architecture enthusiasts will appreciate the Cubist-influenced facade. Rooms have amenities for the many business travelers passing through, but mid-century details keep it from feeling too corporate. As does the expansive rooftop bar.
127 W. Huron St.
Chicago, IL 60654
+1-312-649-2000
An artsy enclave in the gallery-heavy River North neighborhood. The award-winning bar, hotel-grade mattresses, and roster of special events will make you think twice about calling it a hostel.
19 E. Ohio St.
Chicago, IL 60611
+1-312-940-3699
The historic hotel (once host to legends like Al Capone) makes a laid-back comeback with cozy, if slightly kitschy, interiors reminding guests that we are in the Midwest after all. Local artwork dots the lobby and rooms — pick an east-facing room for Lake Michigan views.
1816 N. Clark St.
Chicago, IL 60614
+1-312-254-4700
In the bustling Wicker Park neighborhood is the city's newest hotel in the former deco Northwest Tower. Rooms are warm and bright thanks to the triangular architecture of the building. The Hollander, the sister property next door, caters to the social media-minded by connecting guests online before their stay at the hotel.
2018 W. N. Ave.
Chicago, IL 60647
+1-872-315-3050
Far enough from the crowded downtown Loop, but near enough to Magnificent Mile shopping and the lake, the modern Gold Coast hotel manages to be equally luxe and accessible. No need to check out early; Nico Osteria has an excellent breakfast menu. And make use of the complimentary luxury car service.
21 E. Bellevue Place
Chicago, IL 60611
+1-312-266-2100
The Venetian Gothic landmark opposite Millennium Park received a recent Roman and Williams facelift — look out for playful re-imagined vintage furnishings (like a pommel horse-turned-bench), Carrara marble bathrooms, and boxing-style robes. If you ever find yourself in Chicago in winter (why would you do that to yourself?), cozy up in the library by 19th-century fireplaces and end the night with drinks at the historic Cherry Circle Room.
12 S. Michigan Ave.
Chicago, IL 60603
+1-312-940-3552
If you don’t want to stay at a big hotel, it doesn’t get cooler than this six-room Logan Square inn, a favorite of musicians and interesting wanderers. The style is vintage and the prices (from $85/night) are unbeatable. The bar pours stiff cocktails and the kitchen turns out incredible, meat-heavy dishes. The vibe is easy, loud, and, on most days, plaid.
2657 N. Kedzie Ave.
Chicago, IL 60647
+1-773-276-7110
A hotel that’s equal parts French chic and French sleek, from the striking architecture to the cocktail lounge. The hotel may be big, but the rooms feel like sanctuaries.
20 E. Chestnut St.
Chicago, IL, 60611
+1-312-324-4000
The rooms (standard, lofts, and suites) feel like apartments, with ample room for dining, working, and relaxing, which you can also do on-site at David Burke’s Primehouse, the gym, and the spa. Art is a key feature throughout: The James collaborates with local galleries and museums on the works shown.
55 E. Ontario St.
Chicago, IL 60611
+1-888-526-3778
The rooms are massive, as befits a hotel that does everything in grand, yet understated, style. Service is attentive; amenities are cutting-edge. The rooftop spa has an outdoor deck and pool.
108 E. Superior St.
Chicago, IL 60611
+1-866-382-8388
At the River North boutique hotel, the rooms are stylish and inviting and the bathrooms are oversized. The amenities are top-notch, from bedding and Wi-Fi to the 24-hour fitness center and the gorgeous indoor pool on the 17th floor.
505 N. State St.
Chicago, IL, 60654
+1-312-755-9703
So much to love. The lake and city views, the Magnificent Mile location, the contemporary art and design throughout, the soaking tubs, the chic NoMI Kitchen, lounge, and garden.
800 N. Michigan Ave.
Chicago, IL 60611
+1-312-335-1234
The thrifter's dream store is in a decommissioned 1920s-era Calo Theater. In support of Howard Brown Health Center, the consignment store brings in used and vintage goods of the highest quality. And if you need a break from sifting through the racks, the furniture section in the center of the room makes for a great resting spot.
5404 N. Clark St.
Chicago, IL 60640
+1-773-388-1600
Recently reopened in a cozier spot in Lincoln Park after a decade in Old Town, the stationery shop is filled with some of the best paper goods in the market right now from global designers and lesser-known local artists. If you're lucky, owner Chandra Greer might be manning the till when you stop by; she'd be more than happy to offer recommendations.
1013 W. Webster Ave.
Chicago, IL 60614
+1-312-337-8000
Thousands (like more than 40,000) of domestic and imported vinyl available in all formats and speeds. There are brand new titles, collector albums, and tons of vintage finds. The dedicated (with patience and hours to spare) should head to the back for the "cheapie" bins.
2604 N. Clark St.
Chicago, IL 60614
+1-773-929-6325
A super fun, quirky, very arty Wicker Park bookstore that assembles avant garde, soft-core porn, design junkie ‘zines, and great fiction in one place, and hosts readings and events with their creators.
1854 W. North Ave.
Chicago, IL, 60622
+1-773-342-0910
The Bucktown shop may look antique-chic, but the designers are cutting edge and very carefully curated by Robin herself. There’s no sign at the entrance but rather a sculptural wire ball.
2108 N. Damen Ave.
Chicago, IL 60647
+1-773-278-6150
Nice people selling cool products for the home – furniture, accessories, custom pieces – in an charming setting. Have you died and gone to retail and design heaven? Quite possibly.
1052 W. Fulton Market
Chicago, IL 60607
+1-312-432-0100
An indoor-outdoor vintage extravaganza comprised of several markets – Chicago Antique Market, Indie Designer Market, Modern Vintage Chicago, and Holiday Market – held on a handful of weekends throughout the Fall. More than 200 merchants sell clothes, furniture, music, food, and more. Great for the people-watching, too.
1340 W. Washington Blvd.
Chicago, IL 60607
+1-312-666-1200
A cornucopia of eco-friendly, minimalist high-quality home textiles -- bedding, pillows, table linens -- inspired by the husband-and-wife team’s time in Finland. Charming and minimalist accessories include candle holders, vases, and cute sculpted owls. Open Wednesday-Friday.
2000 W. Fulton St.
Chicago, IL 60612
+1-877-492-7960
The ultimate high-fashion boutique in Chicago, with women’s clothing and accessories from designers like Alexander McQueen, Proenza Schouler, Jean-Paul Gaultier. A total Vogue roll call, in other words, in a striking red space. Is the First Lady still a customer? Owner Ikram Goldsmith is too discreet to dish.
15 E. Huron St.
Chicago, IL 60611
+1-312-587-1000