💕 Romantic Chicago Staycation Itinerary

You don’t need to leave the city—or even book a flight—to experience a dreamy, romantic getaway. Tucked between skyline views and candlelit corners, Chicago offers countless ways to slow down, reconnect, and make new memories with your favorite person. From luxurious hotels and rooftop mock-cocktails to intimate dinners and hidden gardens, this staycation is designed for couples who want the charm of a destination trip—without the travel stress. Whether you're celebrating a special milestone or just craving quality time, this two-day itinerary will help you fall in love with the city—and each other—all over again.

A 3-Day Escape for Two Without Leaving the City

🌇 Day 1: Sunset, Skylines & Intimate Dining

🏨 Check‑In at a Romantic Hotel

All options are open and welcoming guests:

1.      The Publishing House B&B (West Loop)

  • Address: 108 N May St, Chicago, IL 60607
  • Status: Still operating as a boutique bed & breakfast
 2.      The Langham Chicago
  • Address: 330 N Wabash Ave, Chicago, IL 60611
  • Status: Fully open with Chuan Spa, indoor pool, and rave reviews for service and comfort 

🌆 Sunset Activity

Cindy’s Rooftop – atop Chicago Athletic Association Hotel

  • Address: 12 S Michigan Ave, Chicago, IL 60603
  • Hours: Mon–Thu 11 a.m.–11 p.m.; Fri 11 a.m.–midnight; Sat 10 a.m.–midnight; Sun 10 a.m.–11 p.m. Reservations available—views of Millennium Park and Lake Michigan 

Evening Architecture Cruise

  • Departs near Michigan Ave Bridge / 112 E Wacker Dr. Scenic, romantic river tours available nightly.

🍽️ Romantic Dinner Options

Geja’s Café – Fondue & live flamenco guitar

  • Address: 340 W Armitage Ave, Chicago, IL 60614
  • Hours: Wed–Sun evenings (4–8:45 p.m.); closed Mon–Tue 

Elske – Michelin-starred Scandinavian cuisine with a garden

  • Address: 1350 W Randolph St, Chicago, IL 60607
  • Status: Open and reservation recommended

☀️ Day 2: Slow Mornings & Serene Escapes

🥐 Breakfast or Brunch

  • Maison Marcel – 3114 N Broadway, Chicago, IL 60657
    • Sunny French café with pastries and light fare (open).
  • Do‑Rite Donuts – 50 W Randolph St, Chicago, IL 60601
    • Gourmet grab‑and‑go donuts and coffee (open).
  • Lula Café – 2537 N Kedzie Blvd, Logan Square, IL 60647
    • Cozy brunch spot with seasonal dishes (open).

🌿 Nature Walk or Picnic

  • Alfred Caldwell Lily Pool – 125 W Fullerton Pkwy, Chicago, IL 60614
    • A serene, hidden garden; open seasonally (spring–fall).
  • Garfield Park Conservatory – 300 N Central Park Ave, Chicago, IL 60624
    • Open year‑round with tropical indoor gardens (operational).

Picnic Provisions:

  • Foxtrot Market – 912 W Randolph St, Chicago, IL 60607 (open).

🧖 Spa & Relaxation

AIRE Ancient Baths – 800 W Superior St, Chicago, IL 60642

  • Status: Soulful spa experience open: thermal pools, candlelit tradition, couples massages 
  • Note: Occasional maintenance closures (May) but open for June bookings 

🍝 Dinner & Wholesome Evenings

  • Bavette’s Bar & Boeuf – 218 W Kinzie St, Chicago, IL 60654 (open)
  • La Scarola – 721 W Grand Ave, Chicago, IL 60654 (open).

🗓️ Day 3: Art, Lake Views & Cozy Corners

🖼 Morning: Artistic Immersion

The Art Institute of Chicago

  • 📍 111 S Michigan Ave, Chicago, IL 60603
  • 🕒 Open daily from 11 a.m.–5 p.m. (Early entry for members at 10:00 a.m.)
  • 🧡 Explore Impressionist galleries, the Modern Wing, and the peaceful South Garden for a quiet moment together.
  • 🎟 Admission: $32 adults, free for IL residents on certain weekdays—check site.

🌼 Alternative (if you want something more offbeat):


Museum of Contemporary Photography – Small, intimate, and thought-provoking.
📍 600 S Michigan Ave | Free admission

🥪 Midday: Lunch & Lakefront Walk

Lunch at Picnic Goat (Newer romantic café option in the Gold Coast)

  • 📍 1120 N State St, Chicago, IL 60610
  • 🕒 Daily 9 a.m.–3 p.m.
  • 🥗 Light, fresh, and romantic setting with seasonal fare.

Walk Along the Lakefront Trail

  • Start at Oak Street Beach (just a few blocks away), stroll south toward the Museum
    Campus, or stop near Olive Park for skyline views and quiet benches.

🧺 Alternative: Pack a lunch or pick up sandwiches from Hannah’s Bretzel (233 S Wacker Dr) and picnic lakeside.

🎨 Afternoon: Shared Creativity

Chicago Ceramic Center – Take a casual couple’s ceramics workshop

  • 📍 2418 W 14th St, Chicago, IL 60608
  • 🎨 1.5–2 hour sessions available on select days
  • 🧡 Create something together—perfect for a fun, hands-on memory
  • www.chicagoceramiccenter.com Check schedule in advance—some sessions sell out quickly.

🧵 Alternative:

Lillstreet Art Center – Pottery painting, jewelry making, or couples' drawing classes

  • 📍 4401 N Ravenswood Ave, Chicago, IL 60640

🍰 Sweet Endings: Dessert & Wind‑Down

Dessert Date at Sweet Mandy B’s

  • 📍 1208 W Webster Ave, Chicago, IL 60614
  • 🕒 Open daily from 9 a.m.–8 p.m.
  • 💛 Grab cupcakes, banana pudding, or cookies for a nostalgic, heartwarming treat. Cozy up at a corner table or take sweets to-go for a final lakeside bite.

💖 Optional Evening Wind-Down

  • Chicago Magic Lounge (non-alcoholic seating available with notice)
    📍 5050 N Clark St | Sleek 1920s-inspired venue with magic shows—surprisingly romantic and unique.
  • Harold Washington Library Center Winter Garden –
    📍 400 S State St | Ends earlier in the day (~5 p.m.) but a magical and quiet final stop. 

💡 Bonus Add-On Ideas

  • Private dining experience: Gourmet take-home kit from Monteverde or Publican Quality Meats.
  • Love letters: Write in Art Institute South Garden (111 S Michigan Ave) or cozy up at Sawada Coffee (112 N Green St).
  • Nightcap Alternative: Share a mocktail or dessert at Cindy’s Rooftop terrace (already in itinerary).

📚 Sources & Links

                                                                                                                                                                                                        
Tisha Jones, owner of E Jones Travel, specializes in cruises, family trips, getaways, accessible travel, and budget-friendly adventures.  Whether it's your dream vacation or a quick escape, Tisha offers expert guidance and personalized service.

Comments

Post a Comment

Popular posts from this blog

Tips to Travel with your Kids in Upcoming Summer Vacation

Image
Summer vacation is a perfect time for family adventures. It will help you create lasting memories as well. However, most parents face the challenge of keeping their little ones entertained during long journeys. Read on and let’s take a look at a few tips to travel with your kids this summer and have a quality time. Take Time to prepare Your summer vacation starts before you even leave home. This is when you should create travel packs for each child with age-appropriate activities. You may include coloring books, stickers, small puzzles, and a special toy saved specifically for the journey. This element of surprise goes a long way in capturing your children's attention. Don’t Ignore the Power of Snacks You should never underestimate the entertainment value of snacks. Pack a variety of healthy options such as fruits, cheese sticks, and granola bars in individual containers. Then you can allow your kids to have their own snack bag to manage. For summer travels, you may freeze ...
Read more

The Best Food Destinations in the United States w/Suggested Restaurants

Image
A cross-country culinary tour through America’s most flavorful cities. Introduction Few things reflect the soul of a place like its food. In the United States—a nation shaped by waves of immigration and regional diversity—each city tells its own story through what’s on the plate. From smoky ribs in Texas to gumbo in Louisiana and bagels in New York, this is a country defined by flavor. Whether you’re dining on a dime or sitting down to a more refined meal, the U.S. offers unforgettable food experiences at every budget. Here’s your guide to the top culinary cities in America, along with go-to spots for both moderate and affordable eats. 1. New Orleans, Louisiana A soulful fusion of Creole, Cajun, French, and African influences, New Orleans is a haven for spice, seafood, and deeply rooted culinary traditions. Must-Try Dishes: Crawfish étouffée, jambalaya, gumbo, beignets Moderate: Cochon – A rustic yet refined eatery serving elevated Cajun Southern dishes using locally sourc...
Read more

Why Fall Is the Smartest Season to Travel

Image
Autumn is quietly the travel world’s best-kept secret: a season where scenery brightens, schedules quiet down, and your travel dollar stretches farther. Below I’ll walk through the sound reasons—backed by industry and government data—why fall (roughly September through November in the U.S.) routinely outperforms summer and high-holiday travel for value, comfort, and experience. Why it's better . . .  Traveling in fall tends to give you lower crowds , better prices , and more comfortable weather —plus a bundle of quality-of-experience bonuses (easier reservations, seasonal events, better wildlife and photo conditions). These aren’t just wishful thinking; they’re shoulder-season patterns documented by travel-data firms, tourism authorities, and climate records.[1][2][3] 1) Lower crowds = better experiences Downtown Chicago Summer and major holiday windows concentrate demand into predictable peaks. In fall, many families and students are back to school and business travel dips; t...
Read more