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.
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.
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:
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.)
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
2 - Our 15th Anniversary Chicago Staycation Itinerary -
Friday:
Check into hotel (we stayed at Talbott Hotel for this trip)
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
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)
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