Chicago is one of my very favorite cities to visit for a quick weekend getaway. The flights from Raleigh are quick and easy, and it is the perfect spot for shopping, sightseeing, and eating through a big city that is walkable and easy to get around via public transportation or a ride share. Here are our tips for a Chicago getaway featuring the best things to do, places to eat, and where to stay!
This post was originally written in May 2019 and has since been updated and recirculated for November 2022.
Chicago Getaway: The Best Things to Do, Places to Eat, and Where to Stay
Chicago Getaway: Things to Do
Browse the Shops in Lakeview
Lakeview is my favorite spot to browse and window shop. Some of my favorites include Wigglyville Pet Boutique, where I picked up some of the dental chews that W & G love so much plus a La Croix squeaky toy for Giz. I spent about an hour browsing all the goodness in Foresided Cards & Gifts. I adore a good gift shop, and this one carries Rifle Paper Co, Chicago themed gifts, and other eclectic items. A good book shop is Unabridged Bookstore, perfect for browsing new titles for a book to read on your flight home.
Grab Coffee & Macaroons at Maison Marcel
This beautiful French bakery was perfect for an afternoon pick me up. I stopped for a cup of coffee for strolling through Lakeview, and I couldn’t leave without macaroons. I could have spent all day in this coffee shop with its airy interior, delicious food, and comfortable seating options.
I love its architecture and landscaping, plus the shops, restaurants, and murals.
Take the Last Architectural Boat Tour of the Day
Take the last architectural boat tour of the day to catch sunset and night time views of the Chicago skyline while learning about the architecture along the river. I have taken this tour a few times before and it never gets old! It is a great way to see the city and learn more about the architecture along the waterfront.
Grab a Drink at the LH Rooftop
For gorgeous rooftop views of the skyline, check out the LH Rooftop Bar! It’s the perfect spot for taking in the scenery and relaxing after a day of exploring.
Walk along the Waterfront and the Magnificent Mile
We spent quite a bit of time walking along the waterfront and Magnificent Mile, taking in the scenery and doing some window shopping on our way into Lincoln Park.
Check out the Bean!
On our way from our hotel to the waterfront, we walked right past Millennium Park so we obviously had to stop by the Bean!
Say Hi to the Animals at Lincoln Park Zoo
My first trip to Chicago included a solo walk through Lincoln Park Zoo for an afternoon and I was excited to bring my zoo-loving partner back. This 35-acre zoo is free to the public and is open 365 days a year.
Chicago Getaway: Best Places to Eat
Enjoy Dinner at etta
While etta is a neighborhood restaurant in River North, the vibe is hip, the food is progressive, and the interior is gorgeous. Order the ricotta pillows to start, and then shared hearth-fired caulilini, a classic wood fired pizza (it comes with burrata!), and the rack roasted oysters (because duh).
Enjoy a Night Cap at Paradise Park Pizza
Such a fun place in Wicker Park. It’s eclectic, has a huge menu, lots of fun design elements, including the twinkle light entry way and the Trailer Park Queen sign. It’s definitely a spot to spend some time eating and enjoying the space.
Have Brunch at Crosby’s Kitchen
Located in Southport, Crosby’s is a perfect brunch spot. I ordered the burger with a side of bacon potato cakes while my friend, Kayd, ordered the veggie burger with fries.
Try the Lobster Deviled Eggs at The VIG Chicago
This gem in Old Town has a laid-back, welcoming vibe with delicious food and drinks. Order the lobster deviled eggs for a starter and the spreads are a delicious option as well. We ordered the ricotta, pistachio, and honey, the pimiento cheese, and the artichoke and kale spreads and all were equally delicious. For supper, I ordered the Southern Fried Chicken sandwich and a side of pimento mac and cheese. Pro tip, the sides are large enough to share.
Have a Leisurely Weekend Lunch at D.S. Tequila Company
A delicious Tex-Mex spot in Boystown. I had their Cobb salad and it was a delicious version of. the old classic. It has a fun vibe and I would go back to try their tacos!
Get Chicago Deep Dish from Lou Malnati’s
You can’t go to Chicago and not get deep dish pizza. Lou Malnati’s is my favorite and a must-try! There are a few locations around the city. And whatever you do, get the butter crust.
Have Breakfast at Grant Park Bistro
Start your day by fueling up at Grant Park Bistro. We ordered the avocado toast and the sausage scramble.
Fuel Up at Old Town Pour House
We popped in here for a leisurely lunch when walking from South Loop to Lincoln Park. Start with the pretzel bites and beer cheese and the Cobb salad is a great option for fueling up for an afternoon of exploring!
Sample the Cocktails and Try the Tacos at Pilsen Yards
This bar centric restaurant offers tasty cocktails, delicious tacos, and unique takes on ceviche in a large, open space! Don’t skip the guac either! I ordered the flautas for my main course and I would 10/10 order again!
Enjoy a Diner Style Breakfast in a Historic Building at Pittsfield Cafe
Located on the first floor of this beautiful building, Pittsfield Cafe has been serving up food since the 1980s. Don’t skip the jalapeño bagel–they are made fresh in house and are delicious!
Chicago Getaway: Where to Stay
This hotel is the perfect spot to call home for the weekend while in the city. It is located right across from Grant Park with beautiful views of Lake Michigan. We stayed in a superior room, which is spacious and includes a work desk, an espresso machine, plus wireless charger and USB outlets. There is a delicious restaurant, Grant Park Bistro, located on the first floor of the hotel that offers both indoor and sidewalk dining. The location is convenient for taking a train from Midway and walking from the Roosevelt stop. It is also walking distance to Millennium Park and the shops along the Magnificent Mile.