Planning your first trip to Chicago? You’re in for a wild ride—especially if you’re staying near UIC (University of Illinois at Chicago), a great base for food, culture, and public transport access. Whether you’re here for deep-dish pizza or skyline views, this 4-day itinerary is packed with local eats, iconic views, and non-touristy gems that’ll give you a real taste of the Windy City.

🗓️ Chicago in 4 Days: The Ultimate Game Plan

Here’s how to make the most of your 5-night stay:

📍Day 1: Get Settled, Go Local Near UIC

Explore the Neighborhood
Start close to home! The UIC area and nearby Pilsen are known for their art, culture, and delicious eats.

• Grab a bite at:

  • Carnitas Uruapan (legendary Mexican carnitas in Pilsen)

  • Al’s Beef on Taylor St for a true Chicago-style Italian Beef

  • Do-Rite Donuts for a quick sweet fix

Evening:

• Take a walk through the UIC campus and Little Italy

• Chill with a drink at The Rosebud or catch local art at Chicago Arts District

🚇 Getting around: Use the CTA Blue Line from UIC-Halsted or buses to explore other neighborhoods. It’s fast, safe, and affordable.

🍕 Day 2: Food Tour + Iconic Views

Must-Try Chicago Foods:
✔️ Deep Dish Pizza – Lou Malnati’s or Pequod’s
✔️ Chicago Hot Dog – Try Portillo’s or Byron’s
✔️ Italian Beef – Al’s Beef or Mr. Beef
✔️ Tavern-Style Pizza – Pat’s Pizza (near Lincoln Park)
✔️ Jibaritos (Plantain Sandwiches) – Borinquen Lounge in Humboldt Park
✔️ Maxwell Street Polish – Maxwell Street Depot near UIC

Afternoon:
Head to 360 Chicago (John Hancock Center) and do the TILT experience for heart-racing views.
Alternatively, visit Skydeck Chicago at Willis Tower and step out onto The Ledge!

Evening Tip:

• Dinner at Girl & The Goat or The Purple Pig for upscale yet fun bites

• Nightcap at LondonHouse Rooftop Bar for stunning skyline views over the river

🎨 Day 3: Culture + Hidden Gems

Morning:

• Explore Chicago’s architecture with a winter boat cruise (yes, they still run!) or walk the Chicago Riverwalk

• Visit The Art Institute of Chicago – even if you’re not a huge museum person, it’s worth it for the impressionist collection alone

Afternoon Offbeat Picks:

• Devon Avenue in West Ridge – for authentic Indian and Pakistani cuisine (get a dosa or biryani!)

• Argyle Street in Uptown – Little Vietnam for pho, bánh mì, and Vietnamese coffee

Night Option:
Catch an improv show at Second City or a live jazz set at Green Mill Cocktail Lounge (Al Capone’s old haunt)

🌟 Day 4: Urban Adventure + Sweet Endings

Morning:

• Stroll through Lincoln Park Conservatory or Garfield Park Conservatory—perfect warm escape in winter

• Brunch at Wildberry Pancakes near Millennium Park

Afternoon:

• Walk around Millennium Park (don’t skip the snowy Bean selfie!)

• Check out the Museum of Contemporary Art or grab a Rainbow Cone from Original Rainbow Cone for a colorful dessert

Evening:

• Final food stop: Hit Portillo’s for a Chicago-style hotdog & chocolate cake shake

• Chill at Navy Pier or check out nearby bars in River North for a lively send-off

🍿 Bonus Bites: Chicago Specialties to Hunt Down

Here’s your Chicago food scavenger list—print it, save it, eat it:

• 🔥 Pizza Puff (look for it at old-school joints)

• 🌽 Chicago Mix Popcorn – Garrett’s is king

• 🍗 Chicken Vesuvio – A garlicky, herby, roasted chicken classic

• 🌈 Original Rainbow Cone – Five-flavor ice cream slice (yes, slice)

• 🌭 Maxwell Street Polish Sausage – Perfect late-night fuel

🚖 Getting Around Chicago: Uber vs Public Transport?

Public transit (CTA trains and buses) is super reliable for most of the city.

• Blue Line connects UIC to downtown and O’Hare

• A Ventra card or the Ventra app makes rides easy

• Ubers/Lyfts are best for late nights or heading to less-connected spots like Devon or Humboldt Park

✨ Tip: Use Google Maps transit directions—they’re accurate and update in real time.

🎒 Final Tips for Your First Visit:

• Layer up in winter—wind chill is no joke

• Book restaurants ahead if you want to try hot spots like Girl & The Goat

• Skip Navy Pier if you’re short on time—go for Riverwalk or Logan Square instead

• Don’t worry about seeing everything. Chicago is meant to be savored slowly—with cheese, spice, and skyline views.