When life gets hectic, a getaway sounds tempting—but sometimes, an exotic trip just isn’t in the cards. Enter the staycation: a perfect way to refresh without leaving town or breaking the bank. If you’re looking to create memorable moments close to home, a staycation in Chicago could be just what you need to relax, recharge, and reconnect.

Curate a Unique Staycation with Stoke

Planning a meaningful staycation doesn’t have to be overwhelming. With Stoke, you have a personal assistant at your fingertips to make every detail shine. Stoke helps you plan a staycation tailored to your partner's unique interests, from personalized dining recommendations to little surprises based on their favorites. Let Stoke take the guesswork out of your planning so you can focus on making the weekend unforgettable.

Why Chicago is Perfect for a Staycation

Chicago offers endless options for both adventure and relaxation, making it a fantastic city to explore with fresh eyes. From iconic attractions like Navy Pier and the Art Institute to hidden gems in local neighborhoods, Chicago is brimming with experiences perfect for a romantic staycation. Plus, staying local means you can splurge a bit more on luxurious touches like fine dining or a high-end hotel without the added expense of travel.

Where to Stay: Chicago’s Best Downtown Hotels for a Staycation

For a truly memorable weekend, consider booking a room at one of Chicago's top hotels, each offering unique charm and upscale amenities:

• The Langham, Chicago – This luxurious riverside hotel is known for its impeccable service and stunning city views. The Chuan Spa onsite is ideal for a relaxing couple’s massage.
• LondonHouse Chicago – Located right by the river, this hotel boasts one of Chicago’s best rooftop bars, perfect for a sunset toast with your partner.
• The Peninsula Chicago – For a classic, five-star experience, the Peninsula offers beautiful accommodations, and its rooftop pool and terrace are hard to beat.

Sample Chicago Staycation Itinerary: Friday to Sunday

Here’s a thoughtfully crafted itinerary to make the most of a Chicago staycation:

Friday Evening: Check-In and Dinner at Girl & the Goat

After checking into your hotel, start the evening with dinner at the acclaimed Girl & the Goat. Located in the vibrant West Loop, this restaurant by celebrity chef Stephanie Izard serves inventive shared plates and has a lively ambiance that’s perfect for date night. Be sure to try the roasted cauliflower and goat empanadas—fan favorites!

Saturday: Explore the City Together

• Morning: Start your day with a walk through Millennium Park to see the iconic Cloud Gate (or “The Bean”) and enjoy the sights of this scenic urban oasis. Afterward, head over to the nearby Art Institute of Chicago to see famous works by artists like Grant Wood and Georgia O'Keeffe.
• Lunch: For lunch, grab a table at Lou Malnati’s Pizzeria, a staple for Chicago deep-dish pizza. It’s an experience all on its own, perfect for sharing!
• Afternoon: Spend the afternoon strolling along the Chicago Riverwalk. You can rent kayaks if you’re up for an adventure, or take a more relaxed approach with an architecture boat tour to learn about the history behind Chicago’s iconic skyline.
• Evening Dinner: End the day with a memorable dinner at Alinea, one of Chicago’s most prestigious dining establishments. Known for its innovative, multi-course tasting menus, Alinea is perfect for couples looking to celebrate a special evening.

Sunday: Brunch Before You Go

No staycation is complete without brunch. Before heading home, stop by Beatrix in River North. Known for its laid-back vibe and delicious brunch menu, Beatrix offers plenty of options, from house-made pastries to unique breakfast bowls. The coffee bar is a must-visit for caffeine lovers!

The Ultimate Staycation Planner: Customize with Stoke

While this itinerary offers a taste of what a Chicago staycation could look like, every couple is unique. With Stoke, you can easily create a completely personalized staycation experience. Stoke keeps track of your partner’s likes, dislikes, and wish lists, helping you plan moments that are sure to make them feel cherished. Use Stoke to discover local events, book romantic spots, and set up thoughtful surprises that match your partner's tastes perfectly.

Make Every Weekend an Opportunity to Connect

A staycation is more than just a chance to relax; it’s an opportunity to strengthen your relationship without the stress of travel. Chicago offers the perfect backdrop for memorable experiences, and with Stoke, you’ll never run out of ideas to keep the spark alive. So whether it’s a weekend in the city or a day trip, let Stoke help you plan moments that matter.

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