At this time of year the weather in the Windy City can be unpredictable, but above all it remains one of the USA’s most beautiful cities. Spectacular architecture, low sun glinting off the lake, and the siren call of a deep dish pizza all exert their magic, but we’ve only got 48 hours, so let’s get out there.
Explore Chicago’s neighborhoods, food and drink, and best spots to visit
Begin your Chicago adventure with the city’s specialty at one of the city’s iconic establishments. This bustling pizzeria serves up the classic deep dish, with the caramelized crust. Lunch is the best option for visitors, as the wait for a table can get lengthy after 5pm. Pro-tip: Lunch specials also include a fountain soda.
Where: 2207 N Clybourn Ave
After you’ve fueled up on deep dish, it’s time to dip into Chicago’s commercial life. Damen Avenue offers plenty of designer stores and chic boutiques to warm up the credit card or keep walking and explore the numerous stores of Wicker Park. If spending is not part of the plan, the 606 trail is a community park on a former rail line, popular with walkers and cyclists, and a great way to sample the Chicago breeze and take in the picturesque cityscape.
Shopping alternatives: Armitage in Lincoln Park or Clark St in Andersonville
Cocktail hour at Danny’s or the Violet Hour
All that shopping and strolling warrants a drink. The Violet Hour offers an elegant, loungey atmosphere, spread across three salons, with a marble bar where you can enjoy a cocktail and people-watch. You could also check out Danny’s, a neighborhood bar, if you’re looking for a less fancy joint with a laid-back vibe.
Where: Danny’s, 1951 W Dickens Ave; The Violet Hour, 1520 N Damen Ave
Health-conscious Chicago gourmets throng to the Diner, meat-free since 1983. Delicious entrees include veggie versions of Thai, Mexican, and Italian classics, alongside meat-free takes on diner classics such as ‘wings’ and ‘steaks.’ Gluten-free and vegan options are abundant.
Where: 2333 N Milwaukee Ave
Dinner alternatives: Green Zebra, Entente, Bad Hunter
Comedy show at The Annoyance or Second City
Chicago is famous for nurturing comics at its stand-up and improv clubs. Take in a show and spot the stars of the future. The Annoyance is a cool theater and bar staging improv, musicals, and sketch shows. The legendary Second City has launched the careers of Tina Fey and Dan Aykroyd among many others, and claims to be the world’s premier comedy club.
Where: The Annoyance, 851 W Belmont Ave; Second City, 1616 N Wells St
Alternatives: iO, The Crowd, CiC, or The Neo-Futurists
Enjoy a stylish start to the day at this elegant café in a vintage art deco building. The walls are lined with eclectic works from the owner’s personal collection, and the menu is a work of art in itself. Breakfast and brunch specials use local, seasonal, and organic produce wherever possible, setting you up for a busy day exploring.
Where: 5020 N Sheridan Rd
Alternates: Mortar & Pestle, 3 Arts Club Café, Southport Grocery
Visitors with kids will need a place to spend a morning, and the zoo ticks every box, including the all-important free admission section. The 35-acre park has been around since 1868. Naturalistic environments offer great conditions for viewing the ever-changing collections of mammals, reptiles, and birds. Highlights include the big cats, bear, and chimps. Pro-tip: During the holiday season, the zoo also offers an evening spectacle of luminous displays known to many as simply “ZooLights.”
Where: 2001 N Clark St
Lunch at Latinicity or Eataly
Check out the spacious food hall at Latinicity with its succulent array of Latin American street food specialties. Alternatively, head for a little European enclave at Eataly, an authentic Italian market, with sit-down restaurants or casual pizza and pasta joints. Plus, it’s right in the heart of the Magnificent Mile where you can shop afterwards.
Where: Latinicity, 108 N State Street, 3rd Floor, Chicago, IL 60602, Eataly. 43 E Ohio St, Chicago, IL 60611
Dutiful visitors will want to pick up a gift or two, and Foursided is the obvious place. The store offers a wealth of vintage, retro, and kitsch items that ooze local charm. It’s a one-stop shop for cards, gifts, frames, and souvenirs.
Where: Various locations across the city
Your last night in town has to be marked with some serious clubbing. Beauty Bar has the décor of a classic late 60s retro beauty salon, with a luxurious, laid-back feel. It’s a stylish place to enjoy a Martini or two and dance the Midwestern night away.
Where: 1444 W Chicago Ave, Chicago, IL 60642
Alternates: Baby Atlas, Holiday Club
There’s so much more to do and see in Chicago than what one can accomplish in 48 hours, but we hope this list gives you a taste of what The Windy City and all of its unique neighborhoods have to offer.