Chicago, Illinois-4-day-itinerary

November 10, 2024

Chicago Itinerary: 4 Days in the Windy City

Morning: Start your day at Millennium Park (free admission) and take a stroll through the beautiful Lurie Garden. Don’t miss the famous “Cloud Gate” sculpture, also known as “The Bean.”
Lunch: Head to Portillo’s (multiple locations) for a classic Chicago-style hot dog or Italian beef sandwich.
Afternoon: Take an architecture river cruise ($80-$100 per person) with Chicago’s First Lady Cruises to learn about the city’s rich history and iconic buildings.
Evening: Check-in at the historic Palmer House Hilton (starting at $150 per night) in the Loop. Enjoy dinner at Girl & the Goat (reservations recommended), a Mediterranean-inspired restaurant from Top Chef winner Stephanie Izard.

Morning: Visit the world-renowned Art Institute of Chicago ($20-$30 per person). Spend a few hours exploring the vast collection, including American Gothic and Nighthawks.
Lunch: Grab a bite at The Berghoff ( Loop location), a historic German restaurant serving classic dishes like schnitzel and sauerbraten.
Afternoon: Relax in Grant Park, which hosts many festivals throughout the year, including Lollapalooza. Take a stroll through the beautiful Buckingham Fountain.
Evening: Enjoy dinner at Xoco (multiple locations), Rick Bayless’s casual Mexican spot serving up fresh, delicious street food.

Morning: Explore the trendy neighborhoods of Wicker Park and Bucktown. Visit Myopic Bookstore, a used bookstore with an impressive selection.
Lunch: Head to Big Star (Wicker Park location) for a gourmet taco or burger in a fun, retro atmosphere.
Afternoon: Visit the Lincoln Park Zoo (free admission), which offers a beautiful setting and a variety of animals. Take a stroll through the adjacent Lincoln Park Conservatory.
Evening: Enjoy dinner at The Purple Pig (Magnificent Mile location), offering creative small plates and an extensive wine list.

Morning: Spend the morning exploring Navy Pier, which offers boat cruises, an amusement park, and entertainment options like the Chicago Shakespeare Theater.
Lunch: Grab a bite at Harry Caray’s Italian Steakhouse (Navy Pier location), serving up classic American-Italian cuisine.
Afternoon: Take a scenic walk along Lake Michigan’s shoreline path, which offers stunning views of the city skyline. Rent a bike and ride along the lakefront trail.
Evening: End your trip with dinner at Alinea (reservations essential), a Michelin three-star restaurant offering avant-garde, experimental cuisine.

‘L’ Train: Chicago’s elevated train system is an efficient way to get around the city. A single ride costs $3, or purchase a Ventra Card for unlimited rides.
Ride-hailing: Uber and Lyft are widely available in Chicago.
Water Taxi: Take a scenic ride along the Chicago River with Wendella Sightseeing Boats.

Weather: Be prepared for unpredictable Midwestern weather. Pack layers, umbrellas, and sunscreen.
Safety: As with any major city, be aware of your surroundings, especially at night.
Tipping: 15%-20% is standard in Chicago restaurants and bars.
Maps: Download the Transit app or carry a map to navigate the city’s grid system.

Willis Tower (Sears Tower): Take in panoramic views of the city from the Skydeck on the 103rd floor ($22-$32 per person).
Chicago Architecture Foundation: Explore the city’s rich architectural history through guided tours and exhibitions.
Wrigley Field: Catch a Cubs game at this historic baseball stadium, even if you’re not a fan.

Enjoy your trip to Chicago!