Weekend Guide to Chicago
From stellar skylines to shoreline sightseeing, Chicago has something to offer everyone. Here are some food & drink concepts and activities that I would recommend to anyone who wants to explore the Windy City in 48 hours, or less.
Hotel Recommendation
Loews Chicago Hotel 455 North Park Drive, Chicago, Illinois 60611
My two-night stay did not disappoint! The superior double is ideal for a Girl’s or Sister Trip. My sister and I were offered a room upgrade when we mentioned that we were visiting Chi Town to celebrate our birthday. The views from our room were absolutely stunning. We were right above Loew’s outdoor rooftop terrace, which made the perfect backdrop for our early morning risings and evening glam sessions. The terrace features a restaurant bar called Streeterville Social. It’s a convenient night cap if you want to keep things relaxed and local while staying at the Loews.
Another highlight of the Loews is how accessible it is to different entertainment venues. Walkability is top priority for me, especially when traveling. The Lowes is just minutes away from attractions like the Musuem of Ice Cream and the Chicago Architecture Center. It’s also just a fifteen-minute power walk from the Cloud gate (the bean) sculpture; 201 E Randolph St. Chicago, IL 60601.
Dining & Coffee
Ralph’s Coffee 750 Michigan Ave, Chicago, Illinois 60611
Ralph’s is certainly more than just a photo-op. The caramel iced lattes were the perfect midday pick-me-up as we strolled through Michigan Avenue.
Starbucks Roastery
Thoughtfully designed and deliciously crafted, visiting Starbucks Roastery is a must if you’re open to experiencing an evolved menu of seasonal blends and hearty bites. The Princi Bakery, located on the second floor of the roastery offers savory pizza options and sweet treats. The raspberry cheesecake was sweet and fresh!
3 Arts Club Café 1300 N Dearborn St. Chicago, Illinois 60610
Luxury not only looks but tastes good. If you’re familiar with Restoration Hardware, you know that it’s a haven for grand showrooms, textiles, and timeless furniture selections. The Chicago location features an upscale restaurant concept and garden courtyard that will leave you feeling enchanted. Top on my list are the signature RH burger, lobster roll, and shaved ribeye sandwich.
Hampton Social 164 E Grand Ave, Chicago, Illinois 60611
Nautical and nice, Hampton on Streeterville has tasty grilled and seafood options like their ahi tuna bowl, and balsamic glazed skirt steak. Yum!
Activities
The Navy Pier 600 E Grand Ave, Chicago, Illinois 60611
The Navy Pier is a historic, vibrant stretch of sit-down restaurants, cultural rides, shops, and more. Experiencing the firework show was super memorable for me this past summer. Click here to see the pier’s ongoing exhibits and weekly events.
Skydeck at Willis Tower 233 S Wacker Dr Ste 4400, Chicago, Illinois 60606
The Skydeck experience will take your breath away. There is no better view that will capture Chicago’s beautiful landscape and promienent skyline. This activity is a great start to the morning. Definitely plan ahead and purchase tickets for their 9am or 10am session.
Chicago River Architectural Boat Tour
I get it—tourist attractions aren’t on everyone’s menu. They can seem redundant or dated. While most would consider the Chicago River boat tour to be an attraction for tourist-types, I would consider it a necessity for anyone who appreciates architecture, history, and priceless views. Photos do not do this boat tour justice! Click here to browse through Chicago’s variety of guided boat tours—from sunset cocktails to historical fun trivia-filled rides.
Thank you for reading! I hope that you enjoy your next trip to Chicago.
Photography captured by me. For more photos & videos, please watch my Chicago highlights on Instagram.
Travel, Food & Drink Guides
