Room Cougar

Your AI trip plan for a family 3 day trip to Chicago, IL for ages 36-50 with a low budget - Activities, Attractions, Cost Saving Tips, Hidden Gems, Restaurants

Day 1: Discover Downtown Chicago

  • Morning:

    • Breakfast at Yolk (Start your day with affordable and hearty breakfast options in the Loop.)
    • Millennium Park (Explore the park's free attractions such as Cloud Gate, Crown Fountain, and Lurie Garden.)
  • Afternoon:

    • Lunch at Big Star (Enjoy budget-friendly tacos and nachos in a lively atmosphere in Wicker Park.)
    • Chicago Cultural Center (Visit this free museum to admire stunning architecture and rotating art exhibits.)
  • Evening:

    • Dinner at Portillo's Hot Dogs (Taste iconic Chicago-style hot dogs and Italian beef sandwiches without overspending.)
    • Stroll along the Chicago Riverwalk (Enjoy a free evening walk with beautiful city views and public art installations.)

Day 2: Explore Local Neighborhoods and Art

  • Morning:

    • Breakfast at Ann Sather (Delight in affordable Swedish pancakes and cinnamon rolls in Lincoln Park.)
    • Lincoln Park Zoo (Visit one of the oldest free zoos in the country, perfect for family fun.)
  • Afternoon:

    • Lunch at Varasiz (Enjoy budget-friendly Mediterranean street food near Lincoln Park.)
    • Chicago History Museum (Learn about the city's rich history with affordable admission rates or free days.)
  • Evening:

    • Dinner at Pequod's Pizza (Indulge in delicious pan-style pizza at reasonable prices in Lincoln Park.)
    • Free Jazz Night at Andy's Jazz Club (Experience live jazz performances with no cover charge on select evenings.)

Day 3: Parks, Lakefront, and Hidden Gems

  • Morning:

    • Breakfast at Lou Mitchell's (Enjoy hearty and affordable breakfast dishes at this historic diner.)
    • Grant Park (Relax in the expansive park, visit Buckingham Fountain, and explore free outdoor spaces.)
  • Afternoon:

    • Lunch at Lemon Inc. (Savor budget-friendly vegetarian and vegan dishes in the West Loop.)
    • Explore the West Loop's Fulton Market District (Discover hidden boutiques, art galleries, and unique street art.)
  • Evening:

    • Dinner at The Chicago Diner (Delicious and affordable vegetarian and vegan options in Lakeview.)
    • Navy Pier Free Events (Attend free events, enjoy the pier's attractions, and watch fireworks on weekends.)
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