Chicago 2 Day Itinerary

July 12, 2024

Chicago 2-Day Itinerary

Willis Tower (Sears Tower): Start your day with panoramic views of the city from the Skydeck on the 103rd floor.
- Address: 233 S Wacker Dr, Chicago, IL 60606
- Hours: 9:00 am - 10:00 pm
The Art Institute of Chicago: Spend a few hours exploring one of the top art museums in the country.
- Address: 111 S Michigan Ave, Chicago, IL 60603
- Hours: 10:30 am - 5:00 pm

Portillo’s: Try a classic Chicago-style hot dog or Italian beef sandwich at this local institution.
- Address: Multiple locations, including 520 W Taylor St, Chicago, IL 60607
- Hours: Vary by location

Millennium Park: Take a stroll through this beautiful urban park and snap photos of the famous “Cloud Gate” sculpture.
- Address: 201 E Randolph St, Chicago, IL 60601
- Hours: 6:00 am - 11:00 pm
Navy Pier: End your afternoon with a visit to this lakefront attraction, featuring boat cruises, an amusement park, and entertainment options.
- Address: 600 E Grand Ave, Chicago, IL 60611
- Hours: Vary by attraction

Girl & the Goat: Enjoy Mediterranean-inspired cuisine at this trendy restaurant from Top Chef winner Stephanie Izard.
- Address: 809 W Randolph St, Chicago, IL 60607
- Hours: Monday - Thursday: 4:30 pm - 10:00 pm, Friday - Saturday: 4:30 pm - 11:00 pm

The Signature Room at the 95th: Cap off your day with a drink and stunning views of the city from the 95th floor of the Willis Tower.
- Address: 233 S Wacker Dr, Chicago, IL 60606
- Hours: Monday - Thursday: 5:00 pm - 10:00 pm, Friday - Saturday: 5:00 pm - 11:00 pm

Lincoln Park Zoo: Visit this free zoo in the heart of Lincoln Park and see over 1,100 animals from around the world.
- Address: 2001 N Clark St, Chicago, IL 60614
- Hours: 9:00 am - 5:00 pm
North Avenue Beach: Take a short walk to this popular beach and enjoy the views of Lake Michigan.
- Address: 1600 N Lake Shore Dr, Chicago, IL 60610

Alinea: Experience avant-garde cuisine at this Michelin three-star restaurant. (Reservations recommended)
- Address: 1723 N Halsted St, Chicago, IL 60614
- Hours: Vary by day

The Magnificent Mile: Take a stroll along this famous stretch of Michigan Avenue and shop at high-end boutiques or visit the Tribune Tower.
- Address: N Michigan Ave, Chicago, IL 60601
- Hours: Vary by store

Au Cheval: Try a trendy burger or diner-style fare at this hip restaurant in the West Loop.
- Address: 809 W Randolph St, Chicago, IL 60607
- Hours: Monday - Thursday: 5:00 pm - 10:00 pm, Friday - Saturday: 5:00 pm - 11:00 pm

The Second City: Catch a comedy show at this legendary improv theater.
- Address: 1616 N Wells St, Chicago, IL 60614
- Hours: Vary by showtime

The Langham Chicago: Enjoy luxurious accommodations and exceptional service in the heart of River North.
- Address: 330 N Wabash Ave, Chicago, IL 60611
Hotel EMC2: Experience a unique blend of art, science, and hospitality in this boutique hotel in the Loop.
- Address: 228 E Ontario St, Chicago, IL 60611

‘L’ Train (Elevated Train): Use the convenient and affordable ‘L’ train system to navigate the city. Buy a Ventra Card for easy travel.
Ride-hailing Apps: Uber and Lyft are widely available in Chicago.

Weather: Be prepared for unpredictable Midwestern weather with layers, umbrellas, and sunscreen.
Tipping: Aim to tip 15-20% at restaurants and bars.
Safety: Avoid traveling alone at night and stick to well-lit areas. Keep valuables secure.
Chicago-style Pizza: Try a deep-dish pizza at Lou Malnati’s or Pequod’s Pizza.
Festivals and Events: Check the city’s event calendar for festivals like Lollapalooza, Pitchfork Music Festival, and Taste of Chicago.

Enjoy your trip to Chicago!