It’s true, our winters are long, and yes, the Cubs are terrible, and ok, maybe our mayor dances like this to Robin Thicke, but Chicago is also one of the most fascinating cities you'll ever meet. It's a city rich in culture, with a vibrant art and design scene, stunning architecture, fabulous cuisine, and historic, walkable neighborhoods. Chicago has its quirks, but it's also an easy place to love.
- The Art Institute of Chicago. Built for the World's Fair of 1893, the stunning Beaux-Arts building houses a permanent collection of close
to 300,000 works. (So inspiring is this museum that both Ferris Beuller and I
spent our afternoons here when playing hookie in high school.) Also check out the
newly constructed Modern Wing and take a stroll across the elevated Nichols
Bridgeway, which leads to the grand lawn of Millennium Park.
- Millennium Park. Once an industrial rail yard, Millennium Park was constructed as a multi-functional, free urban public space. Some highlights to visit are Anish Kapoor’s Cloud Gate, the 5-acre Lurie Garden, and the Frank Gehry-designed Pritzker Pavilion — a great spot to bring a picnic and enjoy a free concert or performance under the stars.
- Chicago Cultural Center. Originally built in the 1890’s as Chicago’s first central library, the Cultural Center is a work of art in itself, featuring a stunning Tiffany dome (word on the street is that it’s the largest Tiffany dome in the world) as well as a second and equally-stunning Healy-Millet dome. The center is free and also offers free art shows, concerts, performances, and lectures.
National Museum of Mexican Art. Located in Chicago’s Pilsen neighborhood, the museum showcases traditional Mexican art and artifacts dating from 3,000 years ago to the present. I especially love their folk art, textile, and photography collections.
- The best way to learn about Chicago’s famous architecture is by taking an architecture tour. You’ll discover hidden architectural gems, and the tour guides cover lesser-known facts and interesting details about some of Chicago’s most famous buildings. Even for the DIY sight seer, these tours are definitely worthwhile. The Chicago Architecture Foundation offers waking tours, river cruise tours (a fan favorite among visitors), bus tours, bike tours, a new photography cruise, and Segway tours (be warned: you may feel ridiculous riding a Segway through downtown Chicago, but that’s probably a universal truth for Segway riding in general).
- Garfield Park Conservatory. For a slice of botanical paradise in the middle of the city, head to Garfield Park Conservatory, a 4.5 acre horticultural center with indoor and outdoor gardens, including a show house, desert house, palm house, a children’s garden, and two grand exhibition halls.
Mies van der Rohe's Farnsworth House. Located in Plano, Illinois (about 60 miles southwest of
Chicago) — a tour of the house and grounds makes for a great day trip from
Chicago. With its continuously uninterrupted glass walls and pastoral setting, Farnsworth
House is considered one of the most comprehensive examples of European
modernist ideals. Purchase tickets in
- Frank Lloyd Wright Home and Studio. Located in Oak Park (just outside of Chicago’s city limits), this was Wright’s personal home and studio from 1889-1909. The tours are informative and offer insight into the origins of Prairie style architecture and Wright’s personal aesthetic. Also in Oak Park and free to the public is the Wright-designed Unity Temple.
- Chicago neighborhoods. Beyond downtown, Chicago is a patchwork of unique, culturally rich and diverse neighborhoods.To really experience the city, I recommend hopping on an L train or bus and heading out of downtown and into a real neighborhood like Andersonville, Logan Square, or Ukranian Village.Take in some local shops, cafes, and stroll down the side streets to take a gander at classic Chicago two-flats, graystones, and bungalows.
- Andersonville. In the last few years, Andersonville has become a hub of home design and vintage shops. Make sure to stop in at Scout to check out vintage items re-imagined in a modern sensibility. Also check out Brimfield, another vintage shop that doubles as a treasure trove of tartan wool. For handmade housewares head north on Foster to Room Service, a great store for mid-century modern pieces and very hip decor items and Haymaker, which recently added a build-your-own-custom-furniture section where customers can craft their own furniture from salvaged wood pieces.
- Neighborly. One of my favorite new home stores, Neighborly carries a wide range of home goods that are modern, functional, and affordable. A wide variety of handmade prints, unique pillows and textiles, and vibrant kitchenware are among the great finds at this delightful shop.
Luminaire. Located in River North (also a great neighborhood
to gallery hop), Luminaire is a massive showroom featuring work from the
world’s top designers.This is an inviting space where visitors are encouraged
to learn, explore and get inspired by great design.
Lincoln Antique Mall. For vintage lovers, this is a fun place to browse, and there's always the possibility of snagging a great vintage piece at a reasonable price. Unique mirrors, lamps, and décor items are nestled among larger furniture pieces.
- Paperish Mess. Part art gallery, part storefront for locally-made goods, and part community space for 75 artists and designers, this is the kind of inspiring place you feel happier after visiting. Check their website for pop-up shops and goings-on, like readings, concerts, and art shows.
- Jayson Home. A home and garden store with a healthy mix of bold, modern, rustic, and industrial. They carry a wide range of furniture and home goods, and they regularly mark down items, so make sure to check the sale goods.
- Orange Skin. A great shop to check out the latest in modern home design — lots of clean lines and vibrant colors to be found here. It’s like the cool friend you have who knows all the newest bands and the best sushi restaurants, but in store form.
- Au Cheval. A modern take on classic diner fare, Au Chevel serves up bold, rich comfort food in a mod-industrial setting. Lauded for their burgers and foie gras offerings, they also make a darn good raw vegetable salad. I know this because I’m the annoying friend who has ordered a salad at a burger bar.
- A tavola. For an intimate, romantic dining experience, A tavola is the place. Situated in an historic brownstone, Chef Dan Bocik has perfected a small menu of regional Italian cuisine, the most famous of which is his gnocchi with brown sage butter. Herbs and vegetables are grown in the restaurant’s back garden, and they now offer cooking classes.
- Ethiopian Diamond. There are a few wonderful Ethiopian restaurants in Chicago, and Ethiopian Diamond is one of them. The sampling menus are a great way to try a variety of hot/cold, spicy/buttery dishes that are eaten with warm injera bread. The communal dining experience makes this a great place to go with a group. Reservations are recommended on the weekends.
- Frontera Grill. Opened twenty years ago by celebrity chef and socially-conscious entrepreneur Rick Bayless, Frontera remains a hot spot for locals and tourists alike. The menu changes monthly and features authentic Mexican cuisine with an emphasis on local, seasonal ingredients. This is a popular place, so reservations are strongly recommended.
- Hot Doug's. I’m putting a hot dog joint on the list because if you’re looking to eat a Chicago-style hot dog, you should eat it here. Anthony Bourdain named it “one of the 13 places to eat before you die.” I guess that pretty much says it all. Just be sure to carve out a couple of hours, as the lines get long (especially on duck-fat-fries days: Fridays and Saturdays).
- Irazu. My friend first brought me to this tiny Costa Rican restaurant ten years ago, and since then the restaurant has become wildly popular while sticking to its roots as a casual, welcoming restaurant that serves homestyle Costa Rican food. The oatmeal shake, ceviche, and El Tica are always amazing. Cash only, no reservations, and weekends are crowded.
- Macku. Modern and breezy sushi restaurant in Lincoln Park. Their signature nigiri, sashimi, and handrolls are inventive and flavorful (try the nama sake and hamachi!). They also serve a variety of delicately tasty soups, such as sweet potato lobster and yose nabe.
- Mana Food Bar. This small vegetarian restaurant in Ukranian Village is brimming with high energy and gorgeous seasonal cuisine. The menu is constantly changing and features both a “hot” and “cold” section, so you can mix and match a variety of small plates to create your own tasting menu. Some highlights are the mushroom sliders, ravioli with almond-mint pesto, baja corn, and caponata. They also have an outdoor patio and great cocktails. I could live here.
- Schwa. If the stars magically align and you can actually get a reservation here (not only because they’re so popular, but also because they don’t answer the phone nor do they have an online reservation system), go. By all means, go. Schwa has been called “Alinea’s punk-rock little brother”, and I think that sounds about right. Chef Michael Carlson and his small crew pour their hearts and souls into dishes like quail egg ravioli, short rib s’mores with campfire smoke, and seared halibut with orange; they also play the music they dig, serve the food themselves, and it’s both Michelin-starred and BYOB, so don't forget to bring a little something for Chef Carlson and his team. It’s an experience you won’t forget.
- Drumbar. Located at the top of the Rafaello Hotel, Drumbar is a downtown rooftop bar that strikes a great balance of stylish yet relaxed.The drinks are inventive and delicious, the bartenders are friendly and helpful, the views of downtown are gorgeous, and the seating is plentiful.
- Green Mill. This legendary jazz club located in Chicago’s Uptown neighborhood was once a hangout for the Chicago mob. In fact, it was Al Capone’s favorite hangout and underneath the club are a series of tunnels he used to smuggle booze during Prohibition. The atmosphere is still 1930’s speakeasy, which makes it the perfect place to sip a cocktail, hear some jazz, and soak up classic Chicago.
- Longman & Eagle. Carefully selected libations are served up at this warm and rustic spot in Chicago’s Logan Square neighborhood. Tasteful but not pretentious, this is a great place for drinks and conversation.
- The Violet Hour. If you’re looking to have your mind blown by a cocktail, this could be your place. Everything here, from the drinks to the decor, is sumptuous. Cocktails are mixed by Master Mixologists (they don’t mickey mouse around here); mixers and add-ins are house made, incredibly fresh, and complicated.
- Delilah's. Delilah's has remained exactly the same since I was 21 (many moons ago). It is, was, and forever shall be, a rock n’ roll bar. Located in Lincoln Park (which is the opposite of rock n’ roll), it’s certainly not a fancy spot, but they also carry too many fine whiskeys to be considered a dive bar. Low-lighting, solid DJs, and free offbeat-film screenings make for a low-key good time.
- Hopleaf. For years Hopleaf has been carrying an impressive selection of craft beers in an intimate, storefront setting. They've recently expanded their space to include additional seating and a lunch menu. Try the Belgium-style mussels and frites alongside your beer. **If you happen to stop in to Hopleaf on a particularly jam-packed evening and aren’t feeling the crowd, walk one block north on Foster to Simon’s Tavern. Simon’s is more old-school Chicago — a long, dark bar with cold beer and a great jukebox. And some nights that’s the perfect combination.
- Hotel Lincoln. I want to pretend I don’t live in Chicago just so I can stay here for a spell. Hotel Lincoln opened its doors a few years ago and I’ve heard only great things about the stylish, comfortable rooms and great service. Some smart and unique offerings include bike rentals available from the locally-made Heritage Bicycles, as well as themed packages, such as a Second City-themed weekend or a Farm-to-Room package.
- The Drake Hotel. One of the grand old luxury hotels of Chicago. F. Scott Fitzgerald, Frank Sinatra, and Princess Diana are a few of the notable figures who've stayed here. The hotel is situated at the top of the Magnificent Mile and offers visitors immediate access to the lakefront and Michigan Avenue. They are also known for their classic high tea, which is served between 1-5 pm in the Palm Court.
- The James Hotel. A newly renovated boutique hotel in Chicago’s Gold Coast. Guest rooms offer clean-lined modernism at its most relaxing. Rooms are decorated using mindful practices, from eco-friendly pillows to organic bath products. The hotel is centrally located near downtown and the River North gallery district, and is also close to CTA trains and buses for easy access to other areas of the city.