How To Spend 48 Hours in Chicago

| © Lucy Hewett
Mason Johnson

Step one of your Chicago two-day itinerary: Bring clothing for every type of weather. Step two: Eat some pizza, go to some parks and museums, put ketchup on whatever the heck you want, and take a selfie at ‘The Bean.’

Two days doesn’t scratch the surface of what the Windy City has to offer, so this list will stick with the tried-and-true experiences that make Chicago unique.

Relax at Millennium Park, which offers 25 acres of greenery, public art and much more

Day one


Sweet delights await you at Panaderia Nuevo Leon, where you can devour mini conchas (sweetbread), gorditas (like a sugary biscuit) and empanadas (a savory pie crust complemented by the sweet taste of cinnamon). Offering fresh food daily, Panaderia Nuevo Leon is best known for its tortillas, which come in several flavors including jalapeño, habanero and mole.

A vendor prepares Mexican food at a street fair in Pilsen, Chicago

Once you’ve overindulged, stroll over to the National Museum of Mexican Art. Curated to represent thousands of years of Mexican culture, the museum embodies the resiliency of the surrounding Pilsen neighborhood, which has stood steadfast against attempted changes and maintained its Mexican heritage. The museum’s broad interpretation of Mexican culture fosters diverse exhibits, like Abyss by painter Rocío Caballero, which creates a dreamlike world that spans the poles of morality, and Show and Tell by photographer Laura Aguilar, which offers a window into her personal life, LGBTQ communities and more.


Hit two birds with one stone for lunch by going to the South Loop’s Flo and Santos for some pizza and pierogi. Not deep-dish pizza, mind you – the city has more to offer. The pizza is thin, crispy and square-cut, which is probably the more common style of pizza found across Chicago. Before the pizza, try some potato-and-cheese or mushroom-and-sauerkraut pierogi, or share some smoked Polish sausage.

An elevated train crosses the Chicago River

Hop on a train north to see the best of what downtown Chicago has to offer. Stop by the Chicago Cultural Center, which boasts some of the city’s most beautiful architecture (no easy feat). Opened in 1897, it started as Chicago’s library, but today, it hosts a mix of free art exhibits. The interior features beautiful marble, and the center is home to a handful of breathtaking glass domes, including a gorgeous Tiffany stained-glass one. And it’s all free to see.

Speaking of free, cross the street to enter Millennium Park. ‘The Bean,’ officially known as Cloud Gate, is a beautiful piece of public art that you’ve probably seen in Instagram photos. Farther east, you’ll find Maggie Daley Park, a gargantuan wonderland of climbing walls, gardens and other whimsical activities, including a skating ribbon open winter and summer (for ice skating and rollerblading, respectively). Hide in this quaint area surrounded in foliage – stuck between the tennis courts and Cancer Survivors’ Garden – and watch the sun set behind the skyline.

Passers-by take photos in front of ‘Cloud Gate,’ nicknamed ‘The Bean,’ at Millennium Park


Keep heading north to Chicago’s Water Tower Place on the Magnificent Mile to end your night with fantastic food, ritzy cocktails and the best views of the city. The Signature Room on the 95th floor of Water Tower Place may not be the highest point in Chicago, but many believe it offers the best views of the skyline. Plus, you can eat the best lobster tail and roasted chicken in the city. After dinner, go one floor higher to sip on cocktails like the passion-fruit mule and blueberries and bourbon. And – this should go without saying – don’t forget to make a dinner reservation.

If you’re somehow still awake, you can attempt to take advantage of Chicago’s rich jazz scene. Uptown, you’ll find the legendary Green Mill Cocktail Lounge. Behind its ritzy neon sign, the Green Mill has an extremely welcoming and casual vibe. You can also head to the South Loop to the Jazz Showcase, which first opened in 1947. For a more modern and sometimes bizarre taste of jazz, you can check out a show at Constellation in West Lakeview. Around the corner from here is the Hungry Brain, which has the same owners as the Constellation but with a dive-bar backdrop.

The Green Mill Cocktail Lounge is a must-see for jazz lovers

Day two


For breakfast on day two, gorge on more baked delights at Cellar Door Provisions. Its menu changes regularly, but if you can try one of its sacred croissants before they’re gone, do so. They’re always fresh and walk a delicate line between flaky on the outside and soft on the inside. Even better is its kouign-amann. This French alt-croissant is a buttery pastry with caramelized sugar covering the bottom and a hint of orange that tantalizes the tongue.

Chicago’s Logan Square neighborhood offers a range of coffee shops, art galleries and trendy eateries

If you take a stroll west, you’ll find Bric-a-Brac Records & Collectibles, which specializes in making its customers point at its products and say, “I had that as a kid!” To the south, you’ll find more shops worth a look, including a great used-book store (Uncharted Books), a great bookstore with new books (City Lit Books) and a great comic-book shop (G-Mart Comics). It’s also worth taking a look inside Wolfbait & B-girls, a shop that sells a mix of clothes, jewelry and other odds and ends, all handcrafted by local artisans.

If you’re too tired to go shopping, you can always rest on a bench in front of the Logan Square “eagle” – a marble column adorned with an eagle. The monument is officially known as the Illinois Centennial Monument and was designed by famous architect Henry Bacon.

Take a break in front of the Illinois Centennial Monument


Down Milwaukee Avenue, you’ll find the Revolution Brewpub, an ideal place for lunch. Known mostly for its Anti-Hero IPA, it also offers other favorites such as the Eugene porter and Cross of Gold ale. If it’s summer, you’ll also be able to try its Rosa hibiscus ale. For food, try the farm-raised beef burger topped with bacon, onion jam and cheddar cheese with a side of hand-cut, seasoned fries. Other highlights include the Kansas-style barbecue pulled pork sandwich and roasted red beet veggie burger.

Hop on the train and head south to the Museum of Science and Industry. A regular crowd-pleaser is its U-505 Submarine Tour. If you’re claustrophobic, you can check out some of the fascinating exhibits, including Wired to Wear, which is dedicated to wearable technology (jetpacks!) or explore some of the amazing, immersive videos, like Oceans: Our Blue Planet and Tornado Alley.

Chicago’s Museum of Science and Industry is one of the largest science museums in the world


If Chicago-style pizza is on your must-try list, there’s a Giordano’s less than a mile away from the Museum of Science and Industry in Hyde Park. With two layers of soft and flaky crust, thick layers of cheese and a heap of sauce on top of it all, the pizza here is definitely overkill, which is probably why Giordano’s, more than any other pizza place, best represents Chicago’s over-the-top personality.

Order a Chicago deep-dish pizza at Giordano’s Pizza, which has been serving the iconic food since 1974

Digest your pizza as you head north where two paths lie ahead of you: dancing or video games.

In River North, you can play NBA Jam with your friends as you sip a stone cold stunner, a whiskey-and-coffee-based cocktail, at Headquarters Beercade. If that doesn’t sound like your scene, you can head back to the Northwest Side to visit Logan Arcade, where you can drink Malört – a local liquor that’s become a practical joke to play on out-of-towners – as you play Addams Family Pinball. Bonus: Logan Hardware also has an old set of the Rock-afire Explosion animatronic band. It’s super creepy to watch these cartoonish, robot animals play the likes of Metallica and The Misfits.

Catch a Cubs game at Wrigley Field

For dancing, you can go to the land of the Cubs and dance at Smartbar. Below the Metro, the popular rock venue vibrates with the sounds of techno and electronic music. To the northwest, tucked away in a quiet part of Bucktown, you’ll find Danny’s. The small dance floor with aged wood caters to dancers and awkward head-boppers alike. DJs play a wide range of music, but expect plenty of soul and beat-driven remixes of classics from the ’60s and ’70s. Wherever you choose to dance, walking out of your chosen venue sweaty with a touch of tinnitus is a pretty good way to end your 48-hour trip to Chicago.

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