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5-Day Chicago Foodie Itinerary for September 2023

  1. Day 1: The Purple Pig
    16 minutes (1.2 miles) from downtown Chicago

    Start your foodie adventure with a lunch at The Purple Pig. A popular spot known for its charcuterie, cheese, and wine, you can indulge in pork neck bone gravy with ricotta and enjoy a glass of wine on their outdoor patio. Spend the afternoon strolling along Michigan Avenue, the Magnificent Mile, and shop around. For dinner, head over to Girl & The Goat, a trendy restaurant that serves modern American small plates and entrees. Finish off your night with a nightcap at Cindy's rooftop bar, located on top of the Chicago Athletic Association.

  2. Day 2: Portillo's Hot Dogs
    30 minutes (7.2 miles) from downtown Chicago

    Start your day with a classic Chicago-style hot dog at Portillo's. The hot dog comes on a poppy seed bun and is loaded with yellow mustard, chopped onions, relish, tomato wedges, a pickle spear, sport peppers, and celery salt. Burn off your lunch with a walk around the beautiful Garfield Park Conservatory. For dinner, head over to Publican Anker, an upscale restaurant that serves American cuisine and seafood dishes. Don't forget to try their famous beer, the Publican Pilsner.

  3. Day 3: Lou Malnati's Pizzeria
    28 minutes (6.5 miles) from downtown Chicago

    Start your day with a deep-dish Chicago-style pizza at Lou Malnati's Pizzeria. This restaurant has been around since 1971 and is known for its buttery crust and fresh ingredients. Spend your afternoon at the Art Institute of Chicago, one of the oldest and largest art museums in America. For dinner, head over to Alinea, a Michelin three-star restaurant that offers an experience like no other. The multi-course menu changes seasonally and showcases Chef Grant Achatz's culinary creativity.

  4. Day 4: The Publican
    20 minutes (1.5 miles) from downtown Chicago

    Start your day with brunch at The Publican. This restaurant serves farm-to-table American cuisine and has an extensive beer list. After brunch, take a water taxi to Chinatown and explore the vibrant community and delicious food. For dinner, head over to Band of Bohemia, a brewpub that serves new American cuisine. Each dish is paired with a beer that is brewed in-house.

  5. Day 5: Little Goat Diner
    11 minutes (0.8 miles) from downtown Chicago

    End your foodie adventure with a breakfast at Little Goat Diner. This retro-style diner serves classic American breakfast dishes with a modern twist. After breakfast, take a stroll along the Chicago Riverwalk and enjoy the views. For your last meal in Chicago, head over to GT Fish & Oyster, a seafood restaurant that offers a wide variety of fresh fish and oysters.

Recommendations

Chicago is home to many food festivals like the Chicago Food Truck Festival and the Chicago Gourmet Festival. If you have time, check out these events for more food options and experiences. A side trip to the nearby city of Milwaukee, Wisconsin is also worth considering as it is famous for its beer and cheese. To maximize your fun, consider renting a bike and explore the city's many bike trails.

Time and Costs Estimates

  • The Purple Pig (2 hours, $60)
  • Girl & The Goat (2 hours, $80)
  • Cindy's Rooftop (1 hour, $30)
  • Portillo's Hot Dogs (1.5 hours, $20)
  • Garfield Park Conservatory (1.5 hours, Free)
  • Publican Anker (2 hours, $100)
  • Lou Malnati's Pizzeria (1.5 hours, $30)
  • Art Institute of Chicago (3 hours, $40)
  • Alinea (3 hours, $500)
  • The Publican (2 hours, $60)
  • Chinatown (3 hours, Free)
  • Band of Bohemia (2 hours, $80)
  • Little Goat Diner (1.5 hours, $20)
  • Chicago Riverwalk (1.5 hours, Free)
  • GT Fish & Oyster (2 hours, $100)
  • Total Estimated Costs: $1140
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