Chicago Staycation Itineraries
Chicago Staycation Itineraries
What is a staycation?
A staycation is a period in which an individual or family stays at home or close to home for vacation activities rather than traveling to a distant location. It typically involves taking time off work or school to relax and engage in leisure activities, but instead of traveling to a different city or country, people explore their own city or nearby attractions. Staycations can include activities such as visiting local landmarks, trying out new restaurants, attending events or festivals, or simply relaxing at home. It's a way to unwind and enjoy leisure time without the hassle or expense of long-distance travel.
Chicago Staycation Itineraries
What are the benefits of a staycation?
Cost savings: Staycations can be much more budget-friendly than traditional vacations that involve travel expenses such as airfare, accommodation, and dining out. By staying close to home, you can save money on transportation and lodging.
Reduced stress: Traveling can be stressful, with factors such as flight delays, lost luggage, and navigating unfamiliar places. Staycations eliminate these stressors, allowing you to relax and enjoy your time off without the hassle of travel logistics.
Exploration of local attractions: Staycations provide an opportunity to discover and appreciate the attractions and activities in your own city or region that you may have overlooked in your daily routine. You can visit museums, parks, restaurants, and other local gems you may not have had time to explore previously.
Flexibility: With a staycation, you have the flexibility to plan your activities according to your preferences and schedule. You can be spontaneous and make last-minute decisions without the constraints of travel itineraries.
Minimal environmental impact: Traveling long distances often involves carbon emissions from transportation, contributing to environmental pollution. Staycations typically involve less travel or use of eco-friendly transportation options, reducing your carbon footprint.
Quality time with loved ones: Staycations offer an opportunity to spend quality time with family and friends without distractions. Whether it's exploring local attractions together, having a picnic in the park, or simply enjoying leisure time at home, staycations can strengthen bonds and create lasting memories.
Support for the local economy: By staying local and patronizing nearby businesses, you contribute to the local economy and support small businesses in your community, which is especially important during times of economic uncertainty.
Overall, staycations provide a refreshing break from routine, allowing you to recharge and rejuvenate without the stress and expense of traditional travel.
Chicago Staycation Itineraries
Planning a staycation can be just as exciting and fulfilling as planning a traditional vacation. Here's a step-by-step guide to help you plan a memorable staycation:
Set Dates: Decide on the dates for your staycation. Block off time on your calendar, ensuring you have uninterrupted days for relaxation and exploration.
Define Goals: Determine what you want to achieve during your staycation. Whether it's relaxation, exploration, or spending quality time with loved ones, clarifying your goals will help shape your plans.
Create an Itinerary: Plan out your activities for each day of your staycation. Consider a mix of relaxation, leisure, and exploration. Research local attractions, events, and activities that interest you and schedule them into your itinerary.
Explore Your Local Area: Take advantage of what your city or region has to offer. Visit museums, parks, theaters, and other attractions you may have overlooked. Check for any special events or festivals happening during your staycation.
Try New Experiences: Use your staycation as an opportunity to try new things. Whether it's sampling cuisine from a different culture, participating in a cooking class, or trying out a new outdoor activity, embrace the chance to step out of your comfort zone.
Plan Relaxation Time: Don't forget to schedule downtime for relaxation and self-care. Treat yourself to a spa day at home, enjoy a leisurely afternoon in the park, or simply curl up with a good book. Remember, relaxation is an essential part of any vacation.
Create a Budget: Set a budget for your staycation to avoid overspending. Consider costs for activities, dining out, and any other expenses you may incur. Look for discounts or deals on local attractions to make the most of your budget.
Prepare Your Home: If you plan to spend time at home during your staycation, take some time to prepare your space for relaxation. Declutter, clean, and create a cozy atmosphere with candles, soft lighting, and comfortable furnishings.
Disconnect from Work: To fully enjoy your staycation, disconnect from work and other obligations. Set an out-of-office message on your email, turn off work notifications on your phone, and resist the temptation to check in during your time off.
Stay Flexible: While it's good to have a plan, stay open to spontaneity and unexpected opportunities that may arise during your staycation. Be flexible and go with the flow, allowing yourself to fully embrace the experience.
Remember, the key to a successful staycation is to relax, recharge, and enjoy the time spent exploring and unwinding in your own backyard.
Chicago Staycation Itineraries
Chicago Staycation Itineraries:
The Chicago Staycation Itineraries I'm sharing in this blog post are all based on our personal experiences and are the actual itineraries we've planned for ourselves. Each staycation has been carefully curated to explore different parts of the city, from boutique hotels to local dining spots and hidden gems we’ve discovered along the way. These itineraries are authentic reflections of how we’ve enjoyed relaxing and exploring our hometown, and I hope they inspire you to plan your own Chicago staycation!
1 - Our 16th Anniversary Chicago Staycation Itinerary-
Friday:
Breakfast at Kasama, a Filipino restaurant of The Bear fame
Morning activity: peruse vinyl records at Dusty Groove
Lunch and Afternoon activity: mini-golf at Puttery
Check into hotel (we stayed at The Ritz Carlton for this staycation.)
Staying at The Ritz Carlton in Chicago offers a luxurious experience with unparalleled comfort and convenience. Located in the heart of the city near the Magnificent Mile, guests have easy access to world-class shopping, dining, and cultural attractions. The hotel boasts stunning views of Lake Michigan and the Chicago skyline, along with elegant, modern rooms and suites. Visitors can enjoy top-tier amenities such as an indulgent spa, fine dining, and a state-of-the-art fitness center. Personalized service ensures every guest feels pampered, making it an ideal retreat for both business and leisure travelers.
Walk around and enjoy the city, get ready for dinner, indulge in some quiet time.
Dinner at Indienne, a one Michelin star Indian fine-dining restaurant
Saturday:
Morning Coffee at Ralph’s Coffee Shop
Breakfast at Tary Coffee House, Kazakh cuisine
Morning activity: the Museum of Contemporary Art
Lunch at Marisol, the restaurant and bar at the Museum of Contemporary Art Chicago
Afternoon activity: a couples massage at The Ritz Carlton Spa
Drinks at Centennial Crafted Beer and Eatery
Dinner and live entertainment at Untitled Supper Club
Sunday:
Coffee at the Starbucks Reserve, go to their third floor for the specialty coffee
Chicago Staycation Itineraries
2 - Our 15th Anniversary Chicago Staycation Itinerary -
Friday:
Check into hotel (we stayed at Talbott Hotel for this trip)
Staying at The Talbott in Chicago offers a blend of boutique charm and modern comfort in the city's vibrant Gold Coast neighborhood. This historic, European-inspired hotel is known for its personalized service and cozy yet sophisticated atmosphere. Guests enjoy easy access to nearby attractions such as upscale shopping on Oak Street, iconic landmarks, and Lake Michigan’s shoreline. The Talbott also features well-appointed, spacious rooms with chic, contemporary design, a welcoming lobby, and an inviting restaurant and bar. Its prime location and intimate setting make it perfect for those seeking a more personalized, unique experience in the heart of Chicago.
Dinner at Sushi by Bou, Gold Coast
Evening activity: The Second City
Saturday:
Breakfast: Room Service, because what a luxury!
Morning activity: the Museum of Contemporary Art
Lunch at Torali, a modern Italian steakhouse at the Ritz Carlton
Afternoon activity: I got my hair done at Dry Bar
Walk around and enjoy the city, get ready for dinner, indulge in some quiet time
Drinks at The Loyalist, the downstairs sibling restaurant to SMYTH
Dinner at SMYTH, a three Michelin star restaurant offering New American cuisine
Sunday:
Breakfast at Pierrot Gourmet, European-style café with excellent quiche
Chicago Staycation Itineraries | Photo by Christina Wilken
3 - A Chicago Summer Staycation Itinerary -
Saturday:
Brunch at The Smith Restaurant
Stroll around the city, especially the river walk
Drinks and people watching at Tiny Tapp Chicago River Walk
Check into hotel (we stayed at The Gwen for this trip)
Staying at The Gwen in Chicago offers a sophisticated, art deco-inspired experience in a prime downtown location. Situated along the Magnificent Mile, The Gwen provides easy access to luxury shopping, dining, and cultural attractions, making it an ideal choice for visitors looking to explore the best of the city. The hotel combines modern elegance with artistic flair, featuring stylish rooms, a rooftop terrace with stunning skyline views, and an upscale restaurant and lounge. Guests can also enjoy exceptional service and exclusive amenities, including a state-of-the-art fitness center. The Gwen’s blend of historic charm and contemporary luxury creates a memorable stay for both business and leisure travelers.
Spend the afternoon on a water Taxi, a great way to spend time on a boat without hefty fees
Dinner at Mako, a restaurant with elaborate, seasonal sushi presentations
Sunday:
Order room service for breakfast and sleep in
Coffee at Big Shoulders Coffee
Walk to our favorite park in the city, Washing Square Spark, for people (but more importantly dog) watching
Return home
Chicago Staycation Itineraries | A Fall Staycation Itinerary for Chicago Open House
4 - A Fall Staycation Itinerary for Chicago Open House-
Friday:
Check into hotel after work (we stayed at the Thompson Chicago for this trip)
Staying at The Thompson Chicago offers a sleek, modern escape with a refined edge, located in the heart of Chicago's stylish Gold Coast neighborhood. The hotel is renowned for its contemporary design, luxurious accommodations, and warm, welcoming ambiance. Guests benefit from close proximity to Lake Michigan, Oak Street Beach, and high-end shopping on Michigan Avenue, making it perfect for both leisure and business travelers. The Thompson also boasts a critically acclaimed on-site restaurant, Nico Osteria, serving fresh Italian seafood, and a chic lounge for cocktails. With personalized service, spacious rooms, and breathtaking views, The Thompson provides an elevated, cosmopolitan experience in one of Chicago's trendiest areas.
Walk to Sparrow for an early cocktail
Walk to the Drifter for light bites and entertainment (pro tip: the Drifter is in the basement of Green Door Tavern)
If you’re still hungry, stop by Indienne for bar bites and a night cap, or make reservations if you want their full tasting menu experience
Saturday:
Wake up early to catch the sunrise over Lake Michigan after stopping at Foxtrot for a coffee and snack to tide you over (the one on Maple is closest to Thompson Chicago)
Walk to the Green City Farmer’s Market for the best selection of flowers and short lines at the most popular stands
Walk to Brass Tack for a heartier breakfast to set you up for a busy day
Spend the day touring iconic buildings with Open House Chicago by the Chicago Architecture Foundation
Wrap up your touring and return to the hotel to freshen up for dinner
Uber to Warlord, plan to arrive around 5, and wait in line until they open for optimal seats
Sunday:
Arrange with your babysitters (I.e. the grandparents) to have your child ready to go around 8:30am
Order breakfast from Stan’s Donuts to be delivered back at your home by the time you arrive
Pack up the car and the entire family and go to Kuipers Family Farms Pumpkin Patch for the morning
Return home, unpack, regroup, grab dinner at Cultivate by Forbidden Root
5 - 40th Birthday Staycation
Creating Art Out of My Life: A 40th Birthday Staycation in Chicago
“I admire that—I think that’s the epitome of living, to be able to create art out of your life.”
— The Swans of Fifth Avenue by Melanie Benjamin
For my 40th birthday, I wanted to celebrate with intention. Not with a grand trip or an elaborate party, but with something that felt deeply personal — a weekend that mirrored the rhythm of my life in Chicago, a city that has given me endless inspiration.
So, I planned an art-and-architecture-themed staycation during one of my favorite weekends of the year: Open House Chicago, the citywide festival that opens the doors to architectural gems rarely seen by the public. The weekend became a love letter to Chicago’s creative spirit — filled with beautiful design, thoughtful meals, and moments of stillness that reminded me that life, when lived with care, really can be its own art form.
Staying at the 21c Museum Hotel
I couldn’t imagine a better place to stay than the 21c Museum Hotel, where art doesn’t just decorate the walls — it defines the experience. From the moment we checked in, we were surrounded by contemporary installations that challenged, delighted, and inspired. Each hallway felt like a gallery; each corner, a quiet invitation to pause and look closer.
There was something profoundly grounding about waking up in a room that doubled as a work of art. The space mirrored my birthday theme perfectly: to live artfully, to blur the lines between the everyday and the extraordinary.
A Taste of Art: Dining Around Chicago
We began Saturday morning with coffee and conversation at OUD Coffee, a serene café tucked away downtown. Between sips of cardamom-spiced lattes, we mapped out our Open House itinerary and watched the city come alive through the window.
Lunch at Bistro Monadnock offered a moment of Parisian calm — crisp linens, quiet conversation, and a glass of rosé that caught the afternoon light just so. Later, we stopped into King of Cups, a tarot-themed cocktail bar that felt like stepping into a velvet-lined secret. I ordered a drink that shimmered like a watercolor, inspired by myth and magic, and toasted to the art of reinvention.
That evening, we dined at Esmé, a restaurant that embodies the very idea of culinary art. Each course arrived like a brushstroke — thoughtful, layered, surprising. The entire experience felt like being inside an evolving exhibition where every plate told a story.
Open House Chicago: Downtown Adventures
Saturday’s itinerary was the heart of the weekend — a journey through Chicago’s most inspiring spaces:
The Arts Club of Chicago: Founded in 1916, it remains a cornerstone of creative conversation. Standing before the restored Mies van der Rohe staircase felt like witnessing the intersection of history and innovation.
The Fine Arts Building: Once a Studebaker carriage factory, now a haven for artists. Each floor hummed with music, murals, and history — proof that art and architecture have always shared the same heartbeat.
The Union League Club of Chicago: A private world of marble staircases and museum-quality art, with docents leading small groups through rooms that whispered stories of the city’s cultural foundation.
Teatro ZinZanni: A theatrical wonder housed in an antique Belgian Spiegeltent — a space where performance and architecture quite literally merge.
The James M. Nederlander Theatre: A breathtaking reminder of Chicago’s cinematic golden age — all gilded domes, carved elephants, and intricate ornamentation.
Hawksmoor Chicago: A restored cable car powerhouse reimagined as a restaurant; we stopped in for a peek at its vaulted ceilings and historic photographs before heading on to dinner.
Every building we visited told a story — of artistry, ambition, and evolution. Together, they formed a tapestry of creativity that made me fall in love with Chicago all over again.
An Artful Souvenir
In between tours, I slipped into Field & Florist and treated myself to a birthday gift: a bottle of FIVE O’CLOCK AU GINGEMBRE by Serge Lutens. It’s a scent inspired by English tea at Buckingham Palace — candied ginger, bergamot, and spice — elegant and quietly confident.
The bottle itself feels like sculpture: minimalist, angular, uncompromising. Much like the city I call home.
A Sweet Discovery
We ended the weekend at Pierrot Gourmet, where I stumbled upon Violet Flame Chocolates, a new creation from Katrina Markoff, the founder of Vosges. Each piece felt like fine art — hand-crafted with rare cacao and botanicals. A reminder that even something as ephemeral as chocolate can tell a story when created with intention.
Looking Ahead
Turning 40 feels less like an ending and more like the unveiling of a new exhibit — one filled with layers, light, and gratitude. This weekend reminded me that beauty isn’t confined to museums or galleries; it’s found in morning coffee, hidden staircases, and the quiet ritual of savoring something exquisite.
Here’s to creating art out of my life — one moment, one building, one birthday at a time.
