Weekend Getaway to Chicago
A few of my friends and I have birthdays within two weeks of each other. So, when it came to celebrating our 30th birthdays, a group trip with my college friends was a no-brainer. My friend Katie took the reins and handled all the planning for our getaway to Chicago. This was my first trip to the Windy City, but it certainly won’t be my last.
If you plan on visiting Chicago, check out the restaurants, bars and attractions that my friends and I explored during our trip.
Trip Duration: Three days of activities (Friday through Sunday), leaving Monday morning
Travel tip: If you fly into Midway, I highly recommend taking the orange line to get into the city. It was much cheaper than an Uber and, depending on when you arrive, you can avoid sitting on the highway in traffic.
Accommodation: SpringHill Suites by Marriott Chicago Downtown/River North
This SpringHill Suites was conveniently located in Chicago’s River North area. We were walking distance from several bars and restaurants, as well as the subway and the “L” train.
Friday
Things to Do: Attend a White Sox Game
The Cubs were in London for a game, so we got tickets to see Chicago’s other baseball team, the White Sox. While Guaranteed Rate Field doesn’t have the hype of Wrigleyville, the upper level of the stadium does boast fantastic views of the city skyline, perfect for snapping some pictures.
I’ll be honest, I really wasn’t paying attention to the game. In fact, I’ve always said that going to a baseball game is a social outing. We spent most of the time taking pictures and catching up with each other. After the Sox took an L, we stuck around for the post-game fireworks.
Travel tip: Take the Red Line to get to the stadium and save money.
Where to Drink: Turtle’s Bar & Grill and Cork & Kerry
After the game, and some brief misdirection from my friend who is a Chicago native, we made our way to Turtle’s Bar & Grill and Cork & Kerry. Both bars were bustling with activity after the game so you can expect a decent crowd with lively people. While each bar also offers food, we put our focus on the drinks and shots, naturally.
Saturday
Where to Drink: Caffe Umbria
Saturday morning, we woke up and ran out for a cup of coffee from Caffe Umbria, which was about a five minute walk from our hotel. An iced lavender latte with vanilla was the drink of choice for many of us on Saturday. On Sunday, I switched to the iced turmeric ginger chai. Since we had brunch reservations, no one ordered food, but there were some very tempting pastries on display.
The cozy café on North Clark Street is located in the historic John R. Thompson Building. While seating is limited inside, there’s an outdoor patio in front of the coffee shop and some seating inside the building.
Where to Eat: Hub 51
One of the main reasons we chose Hub 51 was because of the bottomless mimosa and bellini option. While drinks were the priority, the brunch menu was perfect for our large group. Options range from breakfast selections, such as breakfast sandwiches, eggs benedict and pancakes, as well as salads, sushi, burgers and more.
There was lots of praise at the table for the ahi tuna poke. The nachos came in a massive portion that’s great for sharing. I went with the wagyu smash burger which was a simple and satisfying way to kick off the day.
Things to Do: Explore Navy Pier
Navy Pier is one of Chicago’s top attractions. This waterfront destination features a 200-foot-tall observation wheel, amusement rides perfect for kids and adults alike, restaurants and shops. Navy Pier is also home to free events and public programming, so be sure to check the calendar to see what’s happening while you’re there.
I spent most of my time sipping frosé and strolling the pier. Some friends took a ride on the Centennial Wheel for panoramic views of the city skyline and Lake Michigan. When I do come back to Chicago, I’ll definitely spend more time exploring more of the pier and take one of the sightseeing cruises.
Where to Eat: Gino’s East
I’m sure there’s a longstanding battle over who has the best deep dish pizza in Chicago. We chose the Gino’s East at Magnificent Mile, the flagship location. Our server warned us that there would be a wait for deep dish pizza when we sat down, so my friend and I split an order of the homemade mozzarella sticks while we waited. These were easily the best mozz sticks I’ve ever had.
When it came to deep dish pizza, I kept it simple and split a small cheese. Don’t judge me too hard, I am lactose intolerant and didn’t want to completely wreck my body for the rest of the night. From the tangy sauce to the mouthwatering overflow of mozzarella, this pizza was exactly what I was hoping for. I’m not ashamed to say that I ate my leftovers, cold, before my flight.
Where to Drink: Three Dots and a Dash
If you’re looking for something more than a dive bar, check out Three Dots and a Dash. This speakeasy-style bar has an entrance down an alley, so it can be easy to miss. Inside, take the stairs down to the dimly lit bar area and order one of the tropical-themed drinks.
Three Dots and a Dash provides a unique drinking experience, but you’ll want to be patient. Between the crowd around the bar and the time it takes to craft each cocktail – especially if you order a frozen drink – there will be a wait. If you like a cocktail with a bit of sweetness that’s also tart, try the Vibe Patrol made with tequila, Amaro Montenegro, passionfruit, lime and pineapple. A couple of friends ordered the Poblano Escobar that has a kick of heat from poblano pepper. If you like a frozen, blended cocktail, go with the creamy Banana Daiquiri, garnished with a banana dolphin.
Travel tip: The bar is standing room only, so I recommend making a reservation for a table in advance. They will not let you sit at a table without one, even if there are plenty available.
Sunday
Where to Eat: Lil’ Ba-Ba-Reeba
If you’re traveling with a large group, tapas are always an excellent choice so everyone can get a bit of everything. We really went in when we had brunch at Lil’ Ba-Ba-Reeba, the sister restaurant to Lincoln Park’s Café-Ba-Ba-Reeba. Here’s a quick rundown of everything we ordered for the table: patatas bravas, shaved brussels sprouts salad, deviled egg pintxos, ibérico ham croquetas, Spanish meatballs and the Crystal Bread Tartine Sandwich with soft-scrambled eggs, tomato crudo, avocado and spicy pepper marmalade.
I honestly might be forgetting a few items. The food came out quickly and constantly. We washed everything down with either Bloody Marys or the mango sangria.
Things to Do: Millennium Park
Of course, we had to do the most touristy thing in Chicago – head to Millennium Park and see The Bean. The crowd was moderate when we went, allowing us to get upclose to Cloud Gate aka The Bean for photos. In addition to The Bean, Millennium Park has other sculptures, including Crown Fountain which is a video sculpture that shoots water into a black granite reflecting pool.
Where to Drink: Cindy’s Rooftop
While there is a bar at McCormick Tribune Plaza, you can’t beat the lake views from Cindy’s Rooftop. Situated on the 13th floor, of the Chicago Athletic Association, Cindy’s showcases sweeping views of Millennium Park and Lake Michigan. We grabbed a couple cocktails and headed out to the terrace for photos.
Where to Eat: The Signature Room & Lounge at the 95th
For even more Chicago views, we made reservations for dinner at The Signature Room, perched atop the 95th floor of the skyscraper formerly known as John Hancock Center. I’ll admit, I was skeptical about this choice at first. I was worried this would be a four-star restaurant where you’re just paying for the view. I am pleased to say that I was wrong.
My meal at The Signature Room was well worth the cost. I ordered the roasted lamb chops, medium, which was served with a Greek salad. The chops were so juicy and tender that I couldn’t help myself and had to pick up the bone to get any remaining meat off. The restaurant’s portions were also good, especially if you order the seafood pasta.
The unmatched views were even better during our dinner because there was a post-rainstorm rainbow over Lake Michigan.
Travel tip: If you want to skip dinner and just experience this view with a few drinks and apps, check out The Signature Lounge.