Join us as we explore Chicago with family, balancing local experiences, food adventures, and meaningful time with loved ones. We landed on April 11 and will be in town for 7 days. Here’s our detailed daily itinerary, including meals, cultural stops, and scheduled visits with my dad.
✈️ Arrival Day – Friday, April 11, 2025
- 1:55 PM: Arrive at O’Hare Airport (ORD)
- 2:30 PM: Pick up rental SUV & drive to Jollibee for lunch (📍5033 N Elston Ave, Chicago, IL) – Known for Chickenjoy, Jolly Spaghetti, and Peach Mango Pie
- 4:00 PM: Head to Airbnb and unpack
- 5:30 PM: Grocery run or local essentials (e.g., Seafood City)
- 7:00 PM: Dinner at Lou Malnati’s Pizzeria – Iconic deep-dish Chicago-style pizza
- 9:00 PM: Return to Airbnb to settle in
📆 Saturday, April 12, 2025
- 8:00 AM: Breakfast at Taste of Heaven (📍5401 N Clark St) – Charming café known for scones, coffee, and comfort breakfast
- 9:00 AM–1:00 PM: Visit Dad at Harmony Healthcare & Rehab (📍3919 W Foster Ave)
- 1:15 PM: Lunch at Albany Kebab House (📍4346 N Elston Ave) – Turkish & Middle Eastern plates, family-friendly
- 3:00 PM: Regroup at Airbnb
- 4:30 PM: Explore Downtown Chicago, Lincolnwood Centennial Park, North Shore Sculpture Park
- 7:00–10:00 PM: Family & Friends Dinner (Blocked off)
- 10:00 PM: Back to Airbnb
📆 Sunday, April 13, 2025
- 8:00 AM: Breakfast at Tre Kronor (📍3258 W Foster Ave) – Scandinavian breakfast, cozy and local
- 9:00 AM–1:00 PM: Visit Dad at Harmony Healthcare
- 1:15 PM: Lunch at La Unica Food Mart & Restaurant (📍1515 W Devon Ave) – Cuban & Latin comfort food inside a market
- 3:00 PM: Regroup at Airbnb
- 4:00 PM: Meet Janice for Korean BBQ dinner at San Soo Gab San (📍5247 N Western Ave)
- 6:00 PM: Chill walk or dessert at Somethin’ Sweet Donuts nearby
- 8:00 PM: Back to Airbnb
📆 Monday, April 14, 2025
- 8:00 AM: Breakfast at CornerStone Café (📍2753 N Western Ave) – Locally loved diner with big portions
- 9:00 AM–1:00 PM: Visit Dad at Harmony Healthcare
- 1:15 PM: Lunch at Parachute (📍3500 N Elston Ave) – Modern Korean-American cuisine
- 3:00 PM: Regroup at Airbnb
- 4:30 PM: Visit Montrose Beach or Lincoln Square shops
- 7:00 PM: Dinner at Tanuki Sushi & Grill – High-end sushi experience
- 9:00 PM: Back to Airbnb
📆 Tuesday, April 15, 2025
- 8:00 AM: Breakfast at Lula Café (📍2537 N Kedzie Blvd) – Hip Logan Square brunch
- 9:00 AM–1:00 PM: Visit Dad at Harmony Healthcare
- 1:15 PM: Lunch with Dad at Tre Dita (River North) – Modern Italian-American food
- 3:00 PM: Regroup at Airbnb
- 4:30 PM: Walk at The 606 trail or Humboldt Park
- 7:00 PM: Date Night at Chicago Chop House (📍60 W Ontario St)
- 10:00 PM: Back to Airbnb
📆 Wednesday, April 16, 2025
- 8:00 AM: Breakfast at Old Irving Brewing Co. – Craft brews & brunch plates
- 9:00 AM–1:00 PM: Visit Dad at Harmony Healthcare
- 1:15 PM: Lunch at Demen’s Tap (📍4336 N Milwaukee Ave) – Pub fare & local community vibe
- 3:00 PM: Regroup at Airbnb
- 4:00–8:00 PM: Aimless drive showing in-laws: Lake Shore Drive, Museum Campus, Hyde Park, Humboldt Park, Pilsen, Chinatown, Uptown, and Rogers Park
- 8:15 PM: Casual Dinner at Joong Boo Market Snack Corner – Korean comfort bites
- 10:00 PM: Return to Airbnb
📆 Thursday, April 17, 2025
- 8:00 AM: Breakfast at Over Easy Café (📍4943 N Damen Ave)
- 9:00 AM–1:00 PM: Visit Dad at Harmony Healthcare
- 1:15 PM: Lunch at Big Jones (📍5347 N Clark St) – Southern heritage cooking
- 3:00 PM: Regroup at Airbnb
- 4:30 PM: Optional: Bakery run or park walk
- 6:30 PM: Birthday Dinner at Cebu (📍3120 N Lincoln Ave)
- 9:30 PM: Back to Airbnb
📆 Friday, April 18, 2025 (Departure Day)
- 8:00 AM: Light breakfast at Airbnb or Pho Nam Lua
- 9:00 AM–12:00 PM: Final visit with Dad at Harmony Healthcare
- 12:30 PM: Lunch at Andy’s Thai Kitchen (📍946 W Wellington Ave)
- 2:30 PM: Return to Airbnb to pack and rest
- 3:30 PM: Depart for O’Hare (allowing 4 hours pre-flight for check-in and family)
- 7:36 PM: Flight AA4547 departs ORD for PVD
📝 Notes
- We prioritize spending each morning with Dad and balancing the rest of the day between relaxing family activities and dining at locally loved spots.
- This itinerary keeps us off the typical tourist path and focuses on cultural immersion, great food, and creating memories with family.