Planning your first trip to Chicago? You’re in for an unforgettable ride—especially if you’re staying near the University of Illinois at Chicago (UIC). This vibrant neighborhood is a perfect base with excellent access to public transportation, iconic eats, and lesser-known cultural gems. Whether you’re here for the deep-dish pizza, stunning skyline views, or authentic neighborhoods, this 4-day Chicago itinerary is packed with the best local experiences.

🗓️ Chicago in 4 Days: The Ultimate Game Plan

This 4-day itinerary covers five nights and gives you a mix of classic tourist attractions and authentic local finds. You’ll explore top neighborhoods, try iconic foods, and discover some of Chicago’s coolest hidden corners.

Morning to Afternoon: Explore the Neighborhood

Start your trip by exploring the local vibes near UIC and nearby Pilsen—a vibrant neighborhood rich with Mexican-American culture and art.

Must-Visit Eats:

• Carnitas Uruapan (Pilsen): Legendary for crispy, juicy carnitas served with tortillas, lime, and salsa.
• Al’s Beef on Taylor Street: Home of the classic Chicago-style Italian Beef sandwich.
• Do-Rite Donuts: Grab a quick but unforgettable treat—maple bacon or old-fashioned glazed are favorites.

Evening: Chill & Discover

• Stroll through Little Italy and the UIC campus—great for architecture and people-watching.
• Stop at The Rosebud for a drink and cozy ambiance.
• Explore the Chicago Arts District for local galleries and street art.

Getting Around: Use the CTA Blue Line from UIC-Halsted to zip around. It’s clean, fast, and affordable. Buses also connect to nearby neighborhoods easily.

Morning to Lunch: Eat Your Way Through the City

Start your day with a self-guided Chicago food crawl:

• Deep Dish Pizza: Lou Malnati’s (Downtown) or Pequod’s (Lincoln Park)
• Chicago-Style Hot Dog: Portillo’s or Byron’s
• Italian Beef: Mr. Beef or Al’s again if you’re hooked
• Tavern-Style Pizza: Try Pat’s Pizza
• Jibarito (Plantain Sandwich): Borinquen Lounge (Humboldt Park)
• Maxwell Street Polish: Maxwell Street Depot (near UIC)

Afternoon: Iconic Views

• 360 CHICAGO Observation Deck (John Hancock Center) – Try the TILT experience for a unique view.
• OR
• Skydeck Chicago at Willis Tower – Step onto “The Ledge” and take in sweeping city views.

Evening: Classy Eats & Skyline

• Dinner: Book ahead for Girl & The Goat (West Loop) or The Purple Pig (Magnificent Mile).
• Nightcap: Grab a drink at LondonHouse Rooftop Bar for unbeatable skyline views along the Chicago River.

Morning: Culture Time

• Chicago Riverwalk: Walk or take a winter architecture boat tour (yes, many run in cold weather!).
• The Art Institute of Chicago: Famous for its impressionist collection—think Monet, Van Gogh, and Seurat.

Afternoon: Off-the-Beaten-Path Eats

• Devon Avenue (West Ridge): Discover rich Indian and Pakistani food culture. Grab a dosa or biryani.
• Argyle Street (Uptown): Chicago’s Little Vietnam—don’t miss out on pho, bánh mì, and Vietnamese iced coffee.

Evening: Local Nightlife

• Catch an improv show at Second City—birthplace of stars like Tina Fey and Steve Carell.
• Or, experience old-school Chicago jazz at Green Mill Cocktail Lounge, once frequented by Al Capone.

Morning: Conservatories & Brunch

• Wander through Lincoln Park Conservatory or Garfield Park Conservatory for tropical plant escapes.
• Brunch at Wildberry Pancakes near Millennium Park—expect a wait, but it’s worth it.

Afternoon: Chicago Classics

• Explore Millennium Park: Snap a selfie at The Bean (Cloud Gate), see the Crown Fountain, or just walk in the snow.
• Stop by the Museum of Contemporary Art (great even for non-art folks).
• Dessert: Try the Original Rainbow Cone—a five-layer slice of colorful nostalgia.

Final Evening: Celebrate Chicago-Style

• Final meal at Portillo’s for a hot dog and the famous chocolate cake shake.
• If you still have energy, stroll Navy Pier or go bar-hopping in River North.

Print this list and check off each item:

Public Transit:

• The CTA Blue Line links UIC to downtown and O’Hare.
• Buses are frequent and efficient; use the Ventra card or Ventra app.

Ride-Sharing:

• Uber and Lyft are reliable, especially at night or when heading to less central areas.

Top Tip: Use Google Maps for real-time CTA routes and schedules. It’s accurate and updated live.

• Layer up in winter. The Windy City lives up to its name—dress in warm, windproof layers.
• Reserve hot restaurants in advance. Popular spots like Girl & The Goat fill up fast.
• Skip Navy Pier if you’re short on time. Go for more authentic spots like Logan Square or West Loop.
• Embrace the pace. You don’t have to see everything. Chicago is best enjoyed slowly—with cheese, spice, and skyline views.

Whether you’re here for the food, the views, or the neighborhoods full of character, Chicago welcomes you with open arms (and a hot slice of pizza). From local markets in Pilsen to sky-high views from Hancock Tower, this 4-day itinerary around UIC gives you the perfect taste of what makes the Windy City unforgettable.

Start planning, start packing—and get ready to fall in love with Chicago.