There is nothing like going to a new country for the first time. The cultures, the sights, sounds and smells can hit you like a brick wall, flow through you like a sieve, or fill you like a full-bodied Cabernet. We’d argue that gazing up at a towering skyscraper or staring at your reflection in a metallic art structure in a city park can give you the same feeling. We’ll be honest, if we can’t jet off around the world to new countries every time we decide to take a weekend getaway, at least we can have similar feelings when visiting a new metropolis for the first time.

Chicago, Illinois has been on our list of weekend getaways since we started dating in 2011; we just never got around to it. That is until, the goddess that is Beyonce decided that she would tour with her original gangster husband, Jay-Z. Truth be told, when we agreed that we would travel to see #OTRII (‘On the Run II’ for those not hip enough to keep up with the kids these days) this time around, the other cities on the stadium tour list couldn’t hold a candle to Chicago. Not only did it offer a historic lineup of musicians itself (say Chicago, Kanye West, Fall Out Boy), but it’s also the home to Al Capone, the Chicago Cubs and Wrigley Field, the Chicago Bears and Soldier Field, the Willis (formerly Sears) Tower, Museum Park, the Bean, the Riverwalk–the list just keeps going.

A quick two hour flight from Boston, Chicago towers over the southern shores of Michigan Lake. It’s skyscrapers, though not right on the water, form a dramatic skyline, welcoming first-time guests with an impressive view. The airport is a good 20-25 minute drive from Downtown on a day with little traffic (does this ever happen, Chicagoans?) and it’s quite walkable and easy to get around once in the city center. Most would say that the best time to visit Chicago is in the summer and to avoid winter at all costs; they don’t call it the windy city for no reason. We’d have to agree — we couldn’t imagine what it feels like to be walking through the city with the winds whipping around the buildings at 20-30 mph creating a wind chill of -35 degrees.

Once we arrived at our hotel, the Kimpton Hotel Allegro, we dropped our bags and set off on our first adventure: find deep dish stat. We weaved our way through the grid of office buildings, restaurants, hotels, and apartment complexes until we reached the Chicago River. The greenish water is a magnificent pop of color when photographing the buildings on its bed, like Tribune Tower, the Boeing Building and The MART building; the color is caused by the river’s clay bottom, water from the Great Lake, and algae. Once seated in the famed Lou Malnati’s Pizzeria, we were overcome with excitement for the next three days. This city did not let us down. We can’t wait to visit again to find the hidden gems outside of Downtown!

Keep reading for our itinerary of how to spend 72 breezy hours in the windy city!

72 Hours in Chicago, Illinois

Key Pointers

• Bring comfy shoes, bring comfy shoes, bring comfy shoes. The city is walkable and public transit is easy to navigate. But it’s also deceiving; your destination may be only a couple of blocks from the station, but they are long blocks. And you’ll likely want to stroll around so appropriate shoes are a must.
• If sightseeing is a priority for you, buy a CityPass for your visit. It includes five attractions, including the Shedd Aquarium, the Field Museum, Willis Tower (or Sears Tower), and a choice of Museum of Science and Industry or 360 CHICAGO Observation Deck and either the Adler Planetarium or Art Institute of Chicago. For only $106, you get VIP, fast pass, or express entry to any of the five attractions you choose. Oh and you can take your time to do them; once activated you have nine days to use up all five passes. It’s totally worth it considering the normal price for the Willis Tower alone is over $35.
• If you’re a self-proclaimed foodie, book reservations at your top destinations about a month before heading there. Restaurants like Girl & the Goat and The Purple Pig fill up fast. Do yourself a favor and plan these spots, if only for one night.
• Get up early for some for some of the best photo opportunities. We did this on Friday morning, leaving our hotel room at around 6:30am to head to The Bean. Upon arriving, it was just us and the fashion bloggers. There is nothing really like seeing sights like this intimately and it should be done at least once in a new city.

Where to stay: Kimpton Hotel Allegro: This hotel group is slowly becoming our favorite! From the smell of the lobby to the perfectly sized rooms and the unique, yet modern decor, these hotels have not let us down. And the Allegro was no different. Set three blocks back from the river and two from the nearest metro stop, this hotel is perfectly set in between a few of the famed theaters in Chicago (Chicago theater, Cadillac theater, and Palace theater). The decor mirrors the glamour of these theaters and pays homage to the roaring 1920s with geometric wallpapers, gold fixtures, and bold jewel tones scattered throughout the rooms, lobby, and entrance. We got a great rate by booking about a month out, be sure to add them to your research list!

Where to eat, drink, and be merry:

• Girl & the Goat: The brainchild of Stephanie Izard, a top chef and Beard award winner, this place is marketed as an establishment with ‘bold food with global influence’, which really means your classic favorites inspired by the freshest ingredients in season. Eating at this, or one of her other restaurants, Duck Duck Goat, or Little Goat Diner, is a must.

• Lou Malnati’s Pizzeria: We learned while in Chicago, there are two types of ‘deep dish’ pizza. Lou Malnati’s pizza is known for its flaky, thinner crust. It’s the kind of crust that you can’t help but dip into ranch dressing after taking a few bites of the layers of cheese and meat. There is a debate, even within these Bostonians’ household, as to whether Lou’s or our next place has better pizza.

• Giordano’s: Now both Lou’s and Giordano’s have the same concept of pizza: lots of cheese, delicious fillers like pepperoni and sausage cooked in a deep dish. Where they differ is the crust. While Lou’s has a flaky, buttery crust, Giordano’s is what’s known as stuffed pizza, meaning there is a thicker, doughier crust on the bottom and a thinner crust on top of the cheese and toppings, encasing the pizza toppings and cheese. The best way to know which one you like better, try them both.

• Raised, an Urban Rooftop Bar: One thing to note about Chicago, they love spending time outside in the summer. You can see tourists and city dwellers alike kayaking and biking around the city in the warm months. Knowing this, it’s not surprising the amount of outdoor spaces attached to restaurants; specifically rooftops. Raised is located in the Renaissance hotel on State Street. With its craft cocktails and small plate menu, this place is a hot spot. The views were stunning, even though we were sitting inside. Be sure to add this, or another rooftop to your list if visiting in the summer months.
• Cindy’s: Another hot spot with a view, Cindy’s at the top of The Chicago Athletic Association Hotel on Michigan Ave. Head to the top of this beautiful building for some of the freshest seasonal dishes and a view of Millennium Park and Lake Michigan. Oh and be sure to look up if eating inside or grabbing a drink at the bar, this place is like eating in a greenhouse in the city.

• Buck’s Four Star Grill: Grab a Chicago style hot dog at this summertime favorite located in Grant Park. This outdoor cafe is only open May through September, but offers a great local selection of craft beers and Chicagoan favorites like Chicago style hot dogs, bratwurst sandwiches, cheese curds, and chili cheese fries as well as a unique view of the Buckingham Fountain.

What to do:

• Walk the Riverwalk and see the architecture on foot
• See the buildings and skyline from the water on a Wendella Signature Lake & River Architecture Tour

• Get up early to visit Millennium Park and look at your reflection in The Bean without the crowds

• Walk the city streets and see the marquess of all the historic theaters

• Head out to the Museum of Science and Industry to learn about coal miners in the Midwest or this history of transportation

• Watch the water show at Buckingham Fountain
• Go to Museum Park and walk on the shores of Lake Michigan
• Swim with the fishes, sharks, penguins, and belugas at the Shedd Aquarium

• See a concert or sporting event at the historic Soldier Field
• Head to the top of the tallest building in North America for a bird’s eye view of the Windy City

• Walk to the Field Museum to get up close and personal with some mummies, dinosaurs, and gorillas

• Observe some of the most iconic pieces of impressionist art from Monet, Manet, and van Gogh at the Art Institute of Chicago