The downtown Chicago skyline from Lincoln Park.

There’s something about Chicago that exudes fun and flirty romance, especially in the warmer months. Whether you want an enviable date night, sightseeing that’s good for the soul, or to take in some of the country’s best sporting events, The Windy City has it all. 

Here are six things you and your boo can't miss in Chicago right now. 

Autumn in Chicago is downright beautiful.

Take your love to new heights at Skydeck Chicago

Located atop the world famous Willis Tower, the Skydeck offers unbelievable views spanning up to four states, and creates a lover’s high you won’t forget. Guests can step out on The Ledge, a glass balcony extending four feet outside the 103rd floor so you can take in stunning views of the city 1,353 feet in the air. Pro tip: arrive early or splurge for the fast pass and have your picture-perfect game plan ready, as your experience is timed. 

Float down the river on an architecture tour

The best, and perhaps must touristy, way to experience Chicago is undoubtedly on the Chicago’s First Lady. The tour gives you a unique perspective of the city, with details, trivia and views you’ll swoon over— they also do yoga cruises, twilight river cruises, private events and more—and the two-hour excursion is worth it, no matter how many times you’ve been to Chicago. For daytime cruises, bring sunscreen, hats, and bottled water and get comfy. They have a bar and bathroom on board and you’re sure to get romantic pictures with epic backdrops. 

No visit to Chicago is complete without a visit to the famed Magnificent Mile

Chicago has the word chic in its name, so it stands to reason, shopping is A+. This roughly mile-long stretch on North Michigan Avenue between Oak Street and Chicago River boasts more than 460 premier retailers. Nearby Oak Street offers even more high-end retail shopping. If you’re looking for unique and artsy Chicago shopping, check out Wicker Park/Bucktown. Shopping is just one reason Chicago makes the perfect girl’s weekend.

Visit Lincoln Park

It's a Chicago must-do and while you’re there, try Gemini, an unassuming and casual local American restaurant with a varied menu. It's a made-from-scratch restaurant that's a neighborhood favorite, even for those who don’t live in the neighborhood. Grab an Uber from your hotel, and snag a seat on the pergola-topped sidewalk patio during warmer months, then take a walk around the bustling Lincoln Park neighborhood to walk it all off.

Partake in Chicago's fine dining. 

For an unforgettable experience, with an elegant ambiance and exquisite menu, try Margeaux Brasserie, a Michael Mina restaurant inside the Waldorf Astoria. This award-winning restaurant serves elevated French cuisine in the heart of Chicago's Gold Coast. Located a few blocks from some of Michigan Avenue’s best shopping, it’s the ideal location for the start of a romantic evening.   

Chicago rooftops are reason enough to plan a visit

Streeterville Social, the seasonal rooftop terrace at Loew’s Chicago, has one of the city’s best social scenes, offers gourmet food (lobster rolls), crafty cocktails (the Get Fizzical or Summer Thyme), and sweeping views of the city. Cindy’s Rooftop, inside The Chicago Athletic Association overlooking Millennium Park, is pricier and reservations are a must, but you’ll easily fall in love with this spot, The J. Parker, 13 floors above the Hotel Lincoln, boasts lake views, a retractable roof, frozen drinks, and signature cocktails (like the John Daly’s Wedding rum-based drink). And in River North, Apogee does Avant Garde cocktails amidst an Instagram-friendly rooftop 26 floors up in the Eurostars Magnificent Mile Hotel. Cocktails here are given the same level of detail as a Michelin Star Restaurant, so don’t rush the process. Also, make reservations. 

Where to Stay

We suggest the Loews Chicago, just blocks from the Magnificent Mile with rooms overlooking the Navy Pier that have breathtaking views (ask for the upgrade). The hotel has a convenient, full-service Starbucks in the lobby, and a world-class breakfast at ETA Restaurant + Bar, where you'll find malted pancakes and cauliflower hash on the menu, or lighter options like a banana-coconut smoothie. Plus, they currently offer a Room for Romance package which sets the stage for a romantic, luxurious stay with champagne and chocolate truffles delivered to your room as well as daily breakfast.

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