Your Perfect Chicago Staycation: What to do and where to stay

See recent posts by Hilary Walke

Did you know you can learn Chicago by segway, or tour and taste its chocolate shops, bakeries and cafes? Staycations are the perfect way to feel like you're on vacation while staying local. Discovering your city like you've never seen before is fun, educational and inspiring. Let us help you plan your perfect Chicago staycation.

Where to stay: Hotel Palomar For family-style trips, the Hotel Palomar delivers. They've got welcome gifts for kids, in-room child-safety kits (outlet covers, toilet latches, nightlights), and high chairs and booster seats in the hotel's restaurant. And it doesn't end there -- kids can bundle up in child-size animal print bathrobes, drink "mocktails" during the hosted evening wine tasting, and parents can enjoy babysitting services. Plus, the hotel has an indoor pool, connecting rooms, and a 24-hour concierge service that can recommend kid-oriented activities. Rooms with pull-out sofas and larger suites that can sleep up to five guests make this a perfect pick for families.

Lobby at the Hotel Palomar Chicago

What to do: Chocolate Tours
We’ve all got chocolate cravings. Treat yourself to a 2.5 or 3-hour walking and tasting tour of select Chicago chocolate shops, bakeries and cafe. Public tours are $40 per person, but private tours are also available upon request. You can purchase the tickets online, and there are tours daily, all year round. You can even choose the route: Downtown Loop, Magnificent Mile and Gold Coast, South Loop, etc.
Bonus: Is your craving more pastry-focused? Good news. There are also Cupcake Tours at $50 per person.

What to do: Bike Tour
You can choose from several different bike tours, a great way to explore your city without using gas and getting some exercise. The Lakefront Neighborhoods Tour takes you off the beaten path and onto the quiet neighborhood streets, city parks and beaches. The Night Tours have the same prices, duration and level. It visits the Millennium Park, the Buckingham Fountain, Museum Campus, and more. If you’re looking to include the whole family, the Kid’s Edition is for families with kids 10 and under. The Historic Hyde Park Tour calls for moderate to advanced riders—it covers 24 miles in 4 hours. It’s the only tour allowed to ride past Obama’s former mansion!

Where to stay: Dana Hotel
This adults-only boutique is an urban retreat with zen decor, a spa, a stylish Asian restaurant, and the popular Vertigo Sky Lounge, located three blocks from the Magnificent Mile. The hotel’s serene vibe continues into the luxurious rooms, which feature hardwood floors, large, spa-inspired showers, plush beds, and floor-to-ceiling windows or balconies.

Lobby at the Dana Hotel and Spa

What to do: Chicago Architecture Foundation
The walking tours are unique here — they cover all the modern skyscrapers, historic downtown sites, art deco, “elevated architecture”, Mag Mile, and Millennium Park. There are also boat and bus tours, and the prices vary depending on the tour. The neighborhood walking tours cover Jackson Boulevard, Lincoln Park Architecture, Old Town Triangle, Logan Square, and the Sheffield Historic District. Each tour is guided by an expert docent and they often include interior visits. Most 2-hour tours cost $16 or $15 for non-members; $13 or $10 for students and seniors.

What to do: Segway Tours
Tap into your wild side and hop on a segway for a fun ride. For 2 to 2.5 hours, you’ll see the city on wheels — cruise on the following tours: Lakefront/Museum Campus, Arts and Architecture, Fireworks, or the Taunted Tour. Prices vary from $65 to $60 and there are also private tours.

Where to stay: Trump International Hotel and Tower
This 339-room Trump is one of the top luxury hotels in Chicago, located in a modern glass tower right on the Chicago River and within easy walking distance of the Magnificent Mile. The sleek, glossy decor is subdued and tasteful, and every amenity — from the Michelin-starred restaurant, to the big indoor pool, to bright fitness center, to the spa — is first-rate. The huge, tasteful rooms have limestone bathrooms with soaking tubs and floor-to-ceiling windows (often with phenomenal views). Only The Peninsula can compare.

Lobby at the Trump International Hotel and Spa

What to do: Spa at the Trump, and dinner at the Sixteen
Spend the day being pampered at Trump’s impressive, beautiful spa or dine at Michelin-starred restaurant Sixteen, helmed by Chef Frank Brunacci.

What to do: Head uptown to the Hancock Center: Signature Room, on the 95th floor. You’ll get stunning views, and delicious (if pricey) cocktails and food.

Where to stay: Fairmont Chicago, Millennium Park
This 687-room luxury hotel is in the Loop neighborhood, near Millennium Park and Lake Michigan. Big rooms separate soaking tubs and showers (which even pricier hotels like the Ritz-Carlton lack), iPod docks and 42-inch flat-screen TVs. Add an excellent Asian restaurant, a wine bar, a spa, and stunning design by David Rockwell, and you’ve got one of Chicago’s most luxurious hotels in this price range.

Lobby at the Fairmont Chicago, Millennium Park

What to do: Paddle boarding
Take a one-hour lesson, which includes a 30 minute session with an instructor at $75 per person. You can also engage in some calorie burnings with fitness classes on paddle boards on Lake Michigan at $25/hour.

What to do: Goose Island brewing tour
Claybourn Brewery produces a huge variety of seasonal brews, with over 20 drafts to choose from every day. Food is included in the price: six 4-oz glasses of beer. The tours and tastings are 60-90 minutes each and you must be 21 years of age. Price: $10 per person.

All products are independently selected by our writers and editors. If you buy something through our links, Oyster may earn an affiliate commission.