If I didn’t live in New York (and didn’t have family in Indianapolis) and could pick another US city to move to, I would most likely pick Chicago. To be honest, I almost did several times. The week after I met (my now-husband) Mark I told him I was going to be moving very soon. For some reason, he didn’t run for the hills, and almost 4 years later I still live in New York. (I guess that’s why they call it crazy in love?)
Regardless that I never made the move, Chicago has and will always hold a special place in my heart. Being from Indianapolis, it was the closest “big city” and growing up I made many trips with my family, friends in college for Cubs game (before everyone was a Cubs fan) and even as an adult, it’s still one of my favorite cities to visit.
If you have a choice on time of year to visit, I would most likely try to stay away from winter (there is a reason it’s known as the “Windy City”) but it’s a city with four seasons and even if winter is your only option, the city is magical over the holidays. Just pack a very, very warm coat!
I could make a list of about a thousand places in Chicago, so I’ve done my best to narrow it down. Here are my recommendations for how to spend one day in the Windy City!
521 N Rush St, Chicago, IL 60611
I’ve stayed in a lot of hotels in Chicago and The Gwen is one of my favorites. The moment you walk in to the lobby, you’ll notice the plush couches, gold accents and welcoming rooftop. The River North location makes it easy to walk to restaurants, sights and shopping- which you can access through a walkway in the hotel. (Especially great if you end up visiting in winter or it happens to be raining.) The hotel is a landmarked building with 311 guest rooms and has dining options at Circa Restaurant (Midwestern American) and Upstairs at The Gwen (their rooftop bar perfect for champagne in the summer or Hot Toddys by the firepits in the winter.) Last time I visited they had curling in the winter, and this spring they had glamping. What more could you need? One of my favorite parts of the hotel are the marble bathrooms (with amazing lighting) and their bathrobes. Trust me- I’ve tried a lot of them over the years! This is a perfect place to stay if you’re looking for luxury, glamour and a night out in the city.
160 E Pearson St, at Water Tower Pl, Chicago, IL 60611
This hotel is located at Water Tower Place so you’re in the heart of the downtown when you stay here. The hotel used to be a Four Seasons and went through a huge renovation recently so it feels like you’re in a brand-new hotel. Dining options include Torali (Italian Steakhouse) The Café, a beautiful Club Lounge and a refreshing rooftop in the summer months. If you’re lucky enough to stay one of the days they offer yoga, make sure to sign up, as it’s held on the building’s rooftop 74 floors up. This hidden gem might be the best view in Chicago, as it offers 360* views of the city without waiting in line for admission or pushing your way through a crowd. They also offer a Veuve Clicquot “Champagne on the Water” boat ride experience in the summer, and I can’t think of a better way to see the Chicago skyline, can you? This is one of the most timeless hotels in Chicago and perfect for a chic downtown experience.
Sip and Savor
Chicago may be known for its pizza and hot dogs, but there is so much more to offer when it comes to dining in the Windy City. Every time I visit, I find myself with a whole new list of places to try. If you only have one day in the city, here are my picks for the best of each:
Beatrix Beatrix is part of Lettuce Entertain You, which is the restaurant group that basically owns the city of Chicago. There are a handful of locations, and this is a place I stumbled on my accident on one of my work trips. Beatrix opens at 7 am (which is hard to find sometimes) and has a full coffee bar and bakery in addition to their extensive menu. Do yourself a favor and order the Rainbow Toast- which is sourdough bread with whipped ricotta, pineapple persimmon and blueberries, blackberries and strawberries.
Au Cheval If I had to choose just one, I would most likely name Au Cheval as my favorite burger in the country. This upscale diner in the West Loop is known to have a multiple hour wait, but in my opinion, it’s worth it. I suggest putting your name in an hour or two before you’re actually planning to eat and popping around the West Loop to grab a drink while you wait. The restaurant is small but charming, and one I don’t think should be missed. They’re even open late night in case you find yourself in need of some fancy drunk food. If you don’t have time to wait, the restaurant group has also opened a few offshoot locations called Small Cheval that serves the same burger (or so I’m told) to go.
Intelligentsia Coffee My husband is much more of a coffee connoisseur than I am and this is his favorite place for coffee in Chicago. There are six Intelligentsia locations in Chicago and they have a constant rotation of coffee from South America to Africa. I personally also love their tea selections when I’m not in the mood for a latte.
Goddess and the Baker This cute shop is the perfect place to stop at any point in your day. They serve coffee, breakfast, lunch, dinner and dessert all day and have a few locations around the city. The rainbow latte is Instagram-worthy and the rainbow cake is not only beautiful but tastes amazing as well. They also have several dairy-free dessert options which can sometimes be hard to find.
Girl and the Goat I first tried Girl and the Goat a few years ago for my sister’s bachelorette party. When I returned this summer, it seems that the hype still hasn’t worn off (nor has the very long wait times and reservations that book several weeks in advance.) This is the first restaurant from Stephanie Izard who was the first female chef to win Top Chef and the only chef to win both Top Chef and Iron Chef, so she’s quite a badass if I do say so myself. The food is always consistently great (get the green beans) so I highly suggest making a reservation in advance when planning your trip. Goat Group also has a few other spots such as Little Goat Diner and Duck Duck Goat, which are great alternatives if you need a backup plan.
Cindy’s Rooftop Chicago continues to open more rooftops each season which I love, since nothing makes me happier than a rooftop with good cocktails and great views. Cindy’s was one of the earlier ones to open at the Chicago Athletic Association hotel and still is a staple in my opinion. The venue offers sweeping views of Millennium Park, Lake Michigan and the Art Institute, with both indoor and outdoor options. If you go with a big group, be sure to try the Apothecary Service!
Here are some of the quintessential Chicago sites to see and things to do. Some of these are quick and others could take up your entire day, so depending on where in the city you are, you can decide how much you can explore. I recommend using the train to get around quickly, or when you have time be sure to walk. (Just be prepared for a little wind, no matter the time of year!)
Millennium Park/The Bean (The official name is Cloud Gate, but it’s the giant bean-like sculpture in Millennium Park that reflects the city and is definitely worth stopping by. If you're an early riser, go in the morning before all of the tourists show up.)
Chicago Riverwalk (Located downtown in the Loop, this new path allows you to walk or run along the Chicago River)
Wrigley Field (Wrigley Field is home to the Chicago Cubs and is an experience whether or not the Cubs are in town. If you’re in town for a game day and with a large group, I highly suggest trying one of the Wrigley Rooftops)
Boating on Lake Michigan (Boating on the lake is one of my favorite things to do and an amazing way to view the skyline while enjoying some sunshine.)
Architecture River Cruise (Do it- trust me. It’s much less boring than it sounds)
Second City (This famous comedy club has been around for more than 50 years and is known for alums like Tina Fey, Chris Farley and Bill Murray. They have multiple shows per night ranging from improv to stand up, and always tends to be full. I’ve seen many shows here over the years and they never disappoint.)
Michigan Avenue/The Magnificent Mile
More Than One Day to Wander?
More Hotel Recommendations:
More Breakfast Options:
Little Goat Diner (Comfort Food, West Loop)
Summer House Santa Monica (American, Lincoln Park)
More Lunch Options:
Portillo’s (Chicago-style hot dogs, Multiple Locations)
RL Restaurant (American, Water Tower)
RPM Steak (Steakhouse, River North)
The Hampton Social (Seafood, River North)
More Coffee Options:
Sparrow Coffee (Fulton Street)
Hero Coffee Bar (Multiple Locations)
Caffé Umbria (River North)
Dropshot Coffee & Snack Bar (River North)
Gaslight (Logan Square)
More Sweets Options:
Garrett Popcorn (Multiple Locations)
Firecakes Donuts (Multiple Locations)
Sweet Mandy B’s (Sheffield)
Mindy’s Hot Chocolate (Wicker Park)
More Dinner Options:
Radio Anago (Japanese, River North)
Pacific Standard Time (American, River North)
Lou Malnati’s (Chicago Deep Dish Pizza, Multiple Locations)
Alinea (New American, Ranch Triangle)
The Allis (American, West Loop)
The Publican (American, Fulton Market)
Ema (Mediterranean, River North)
Monteverde (Italian, West Loop)
Aba (Mediterranean, Fulton Market)
Bellemore (New American, West Loop)
Giant (Gastropub, Logan Square)
Bar Biscay (Spanish, West Town)
RPM Italian (Italian, River North)
Pequod's Pizza (Pizza, Lincoln Park)
More Drink Options:
Three Dots and a Dash (Speakeasy Tiki Bar, River North)
The Aviary (Molecular Gastronomy Cocktails, Fulton Market)
3 Arts Club Café (Courtyard in Restoration Hardware, Gold Coast)
RM Champagne Salon (Wine Bar, West Loop)
Goose Island (Brewery, Multiple Venues)
Drumbar (Rooftop, Gold Coast)
Ludlow Liquors (Craft Cocktails, Avondale)
Beatnik (Cocktail Bar, West Town)
Lagunitas Taproom (Brewery, Marshall Square)
More Places to See:
The Ledge at the Skydeck Chicago (The tallest building in the Western Hemisphere, the Ledge is a glass box that extends from the Skydeck. Do not do this if you’re afraid of heights)
Grant Park (Includes the Art Institute, Millennium Park and Buckingham Fountain. Catch a concert if there is one playing)
The Art Institute of Chicago (In Grant Park, the second-largest art museum in the US after the Met)
Museum of Contemporary Art (One of the world’s largest contemporary art museums)
Field Museum (Natural History museum of science with the world’s largest Tyrannosaurus Rex)
Lincoln Park Zoo (One of the oldest zoos, celebrating 150 years, and one of the few that has free admission.)
Did I forget one of your favorite spots? Let me know so I can check it out the next time I'm in the Windy City!