Girls’ Weekend in Chicago: Fun Four-Day Itinerary

My sister and I were coming in from different cities, so we met at the hotel. The Thompson Chicago is an excellent choice. It is located in the Gold Coast neighborhood and within walking distance to all that downtown Chicago offers.

Since we arrived later in the day, we chose to stay in the Gold Coast neighborhood for evening cocktails. The Pandan Chicago features Southeast Asian-inspired menus. You can choose to sit at the bar, where you can watch the bartender mixologist create some beautiful and tasty cocktails, in one of the lounge chairs or on the outdoor patio. Since it’s located on the 18th floor of the Viceroy Hotel, you will enjoy spectacular city views from any spot.

I highly recommend the Red Panda cocktail that has hints of turmeric and ginger!

We started the day with a walk along Lake Michigan and made our way to Cafecito for a Cuban breakfast. The hot chocolate and Cuban coffee were off the charts! Insider tip: You will love it so much that you’ll want to eat here again, so it’s good to know that there are multiple locations throughout the city. Enjoy!

After breakfast, we walked the Magnificent Mile, one of the world’s most iconic shopping districts, where you can enjoy upscale shopping, fine dining and luxe hotels. Take a moment to admire the Burberry building that is made of black stainless steel, monolithic spandrel glass and LED lighting. Admire or stop in the Starbucks Reserve Roastery, the world’s largest Starbucks that is five floors with three-dimensional windows overlooking Michigan Avenue.

Downtown Chicago is an architectural blend of old and new. The skyscrapers and historical buildings are spectacular. We made a stop in these iconic buildings:

• Chicago Cultural Center - See the 38-foot Tiffany Dome!

• London House - Enter the hotel on East Wacker Drive to see the original entrance designed in 1923. Be sure to ride the gold elevator up to the 18th floor for panoramic views of the city. The London House Hotel is the only three-level rooftop bar in Chicago. It’s a great place to take a break for an afternoon snack or cocktail.

From here, we headed back to the hotel to prepare for our Prohibition Speakeasy bus tour, which turned out to be the highlight of our day. This tour was an entertaining way to learn the history of the Prohibition era in Chicago as we visited various neighborhoods and speakeasies in the area. We were able to sip our way through four different speakeasies, ending at Harry Carey’s Italian Steakhouse. Here, we had exclusive access to the basement, which was the headquarters for Frank Nitti, Al Capone’s right-hand man. We were able to see the passageway to Chicago’s underground tunnels and had a photo op in Frank Nitti’s secret underground vault that was used as a mob hideout. This tour was a phenomenal way to learn Chicago’s prohibition and mob history! Insider tip: when you order your drink at Harry Carey's bar, you will be given a bowl of homemade potato chips. They are delicious, and you can bring them to the basement with you!

We had a leisurely start to the day and then headed to brunch at Lil’ Ba-Ba-Reeba, an excellent choice for a girls’ weekend since it specializes in Spanish tapas, pinxtos and sangria! The chorizo-wrapped date pinxtos and hanger steak were my favorites. And the sangria is a must!

From here, we grabbed an Uber and headed to Chinatown. Chicago’s Chinatown is the second largest in the United States, featuring the original Chinatown and New Chinatown. We happened to be in town for the Lunar New Year celebration and parade. This was such a cool experience — one not to miss if you are in Chicago at this time of the year!

After the parade, we joined a Chinatown food and walking tour. The tour takes you to four unique restaurants with authentic tastes at each. It is really worth doing!

After a full day in Chinatown, we headed back to the hotel to freshen up for a night out. We chose to head to the famous Redhead Piano Bar, which is a hot spot for both locals and tourists. So much fun!

We had the morning to find some more architectural gems in the downtown area. This is where we stopped today:

• The Rookery Building - Check out Frank Lloyd Wright’s impressive winding iron staircase!

• Harold Washington Library Center - Head to the ninth floor to see the Winter Garden, a beautiful atrium with marble floors and a 52-foot glass-paneled dome. It’s hard to believe you are actually in a library when you step into this gorgeous space!

• Union Station - You will be impressed by this grand, historic building that is also a national railroad hub. It is worth a visit, even if you are not traveling from the station. My sister caught her train back to Milwaukee here and I headed to the airport.

The weekend was fun and included a great combination of sightseeing, exploring and enjoying Chicago!

Of course, you can’t fit everything into a weekend. Some other hot spots that I highly recommend include:

• Museums - Chicago is home to many fantastic museums. My top favorites: The Art Institute of Chicago, The Museum of Science & Industry, Adler Planetarium, Field Museum, Shedd Aquarium.

• Places to eat - Federales Tacos & Tequila, Girl and the Goat, Quartino Ristorante, Prime & Provisions, Al’s Beef, Lou Malnati’s.

• Places to drink - Three Dots & A Dash, House of Blues Chicago, Green Mill, Kingston Mines, Drake Hotel Lounge Piano Bar, Howl at the Moon Piano Bar, Nobody’s Darling, The Violet Hour.

• Other guided tours - Chicago River 90 Minute Architecture Tour, 360 Chicago Observation Deck, Skydeck Chicago, Chicago’s Favorites Ultimate Food & Walking Tour.