48 Hours in the City of Chicago
Chicago is one of my favorite weekend trips to take because you can really see so much of the city in just a short time. We had a blast exploring the city and of course trying all the foods Chicago is famous for!
What to Do & Where to Eat
Straight from the airport we checked into our hotel and headed to the nearest Portillo’s for hot dogs and cake shakes. Chicago is known for their own style of hot dog, with poppy seed buns, mustard, sweet relish and onions, and Portillo’s is hands down the best place to try one. For a sweet treat, order their famous milkshake with an entire enormous slice of cake mixed in! An absolute must!
Once lunch is done, we headed over to Magnificent Mile to do some shopping and check out the Starbucks Reserve. This was a highlight of the trip! The Chicago Roastery is 5 floors outlining all the best things about the brand and the world’s largest Starbucks. The bottom 3 floors are all about the coffee and pastries, so enjoy a brew and read all about the origins of the company. The 4th floor is for the stronger stuff with a stunning cocktail bar. Highly recommend trying their espresso martini and sitting out on the rooftop (up on the 5th floor). The rooftop has views of Michigan Avenue and is so nice to relax with a drink!
Magnificent Mile is such a nice part of town and the shopping is unreal! Coming from Kansas City, there were so many brands’ outlets that we don’t have here in KC. After scoring the cutest dress and skirt at Zara, we headed to Navy Pier to walk along the shore of Lake Michigan and enjoy the beautiful summer weather. There were so many people out enjoying the day on boats and on the beach. What a unique experience to be out on the water only 100 ft from the city skyline! Navy Pier has all of the classic sights with carnival rides and the iconic carousel! Inside there’s loads of treats and gift shops to find the perfect souvenir.
On our way to dinner we grabbed Italian icees and cut through Millennium Park to see The Bean! Such a classic Chicago site and one you just cannot miss! Even though dessert came first, we knew a late night deep dish pizza was required! Headed to Gino’s for dinner and had the best meal with caesar salads, mozzarella sticks, & the classic Chicago pizza pie.
Started the next day with Brunch at Terrance 16 and explored the city a bit more. Walking along the Chicago River, seeing the Chicago Theatre and grabbing drinks at the Press Room.
Where to Stay
Of course, wanted to be right downtown to get the full Chicago experience! Highly recommend staying at the Embassy Suites Downtown. The perfect hotel with a central location to all of the sights!
Steal my free itinerary below!
