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  1. Feb 14, 2024 · Who needs dimly lit restaurants or romantic getaways when Chicago already has the perfect backdrop to make your valentine feel special? The big picture: There are so many beautiful streetscapes to visit around the city. Here are the top 10 most romantic sections of streets in town. 📍 Alta Vista Terrace (Wrigleyville)

    • Have a romantic and intimate dinner. Restaurants. There’s no shortage of romantic restaurants in Chicago to wine and dine your partner at. You’ll find dimly lit spots, fondue feasts, rooms with beautiful views and many more intimate options.
    • Spend the night at a romantic hotel. Hotels. Planning a romantic weekend away doesn't mean that you have to leave town. In fact, there are so many romantic hotels in Chicago that you probably don't even need to hop in the car.
    • Charter your own hot tub boat with Chicago Electric Boat Company. Things to do. Walks and tours. River North. If you’ve ever been on the Chicago Riverwalk and thought “an open-air, hot-tub boat would really elevate this experience,” then Chicago Electric Boat Company has the perfect date night for you.
    • Take a boozy wine tour at Chicago Winery. Things to do. Walks and tours. Rush & Division. Don't bring wine to the date—bring the date to the wine! Dive into the world of winemaking with guided tours at the Chicago Winery.
  2. May 19, 2023 · The Absolute Best Romantic Things to Do in Chicago [Updated 2024] And with so many options, from stunning skyline views to cozy restaurants and everything in between, it's hard to choose just one! So, I've done the legwork for you and reviewed 12 of the best romantic spots in Chicago.

  3. Jan 13, 2022 · From fine dining to water spas and more, here are the most romantic spots in Chicago. The Press Room. Turn your evening into a speakeasy soiree at The Press Room, an intimate subterranean bar overflowing with magnetism.

    • The Art Institute of Chicago. This world-renowned museum has one of the country’s most celebrated collections of historic and contemporary fine art, including famous works like Edward Hopper’s “Nighthawks,” Seurat’s “A Sunday Afternoon…” and about 300,000 more.
    • The Chicago Symphony Orchestra. Often hailed as one of the best symphony orchestras in the world, the Chicago Symphony performs nearly 100 concerts annually.
    • The Magnificent Mile. The most famous stretch of road in Chicago, the Magnificent Mile is 13 blocks on North Michigan Avenue, filled with world-class shopping, dining, museums, and entertainment venues.
    • CloudBar at 360 CHICAGO. If Chicago at street level isn’t romantic enough for you, try elevating your expectations with a visit to the new CloudBar at 360 CHICAGO Observation Deck.
  4. Looking to impress your special someone? From rooftop dinner and drinks to boat cruises, check out these 13+ Chicago romantic things to do!

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  6. With a plethora of romantic things to do in Chicago, not to mention a swoon-worthy Chicago Skyline, this city is primed for couples on the go. Follow along to find the 36 best things to do in Chicago for couples.

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