Prepare for the adventure of a lifetime to the Windy City, home to the famous Cloud Gate (“The Bean”), Millennial Park and Willis Tower. Whether you’re in town on business or for an exciting family getaway, an action-packed long weekend in Chicago awaits. Explore our Chicago vacation packages and get your bags packed!
Day 1: You have just landed at the bustling Chicago O’Hare International Airport (ORD) and are ready for the trip of a lifetime. There is so much to do, and you fully intend to squeeze as much in as possible in your action-packed long weekend. You will be staying at JW Marriott Chicago so you grab an Uber to get there and drop off your bags so you can hit the pavement. The hotel is centrally located in the city and gives you great access to many of the top tourist attractions. Your first mission is to snag an Instagram shot of the city’s famous Cloud Gate, also known as “The Bean,” so head toward the lake to Millennial Park to have a look. This giant, outdoor, mirrored bean-shape sculpture allows for plenty of fun pictures and videos. After you’ve snapped away to your heart’s content, you continue a tour of Millennial Park and then make your way over to the Lakefront Trail. Located along the shores of Lake Michigan, Chicago’s waterfront presence is one of its greatest assets, and you enjoy fully taking advantage of that. On your way back to the hotel, you walk past the Art Institute of Chicago, where you will be kicking your morning off for day two of your Chicago adventure.
Day 2: It’s bright and early on your second day in the Windy City, and you are on your way to the Art Institute of Chicago — highly regarded as one of the top museums not only in the United States but in the world. You are excited to spend a few hours poking around and exploring this magnificent museum. With more than 300,000 works of art, it would of course be impossible to see everything, but your plan is to take in as much as humanly possible before lunch time! Some of the highlights you’re really looking forward to include “The Bedroom” by Vincent Van Gogh, “A Sunday Afternoon on the Island of La Grande Jatte” by Georges Seurat and “The Old Guitarist” by Pablo Picasso. After a full morning of art, you are looking forward to getting some fresh air and decide to get lunch on Chicago’s Magnificent Mile. After satisfying your hunger, there is lots of exploring to be done in this area, so you wander around taking in all of the shopping and fashion, architecture and other museums. For dinner, Monteverde is home to some of Chicago’s best fresh pasta, so you choose to stop here tonight. When you walk into this bright, airy restaurant, one of the first things you see is the pasta making station, and that is always a good sign! The menu features several Italian classics and also incorporates some of the chef’s modern favorites. Thankfully, Monteverde is only about a mile away from the hotel, so you can roll back there after one delicious meal.
Day 3: It’s your final day in Chicago, so you decide to wake up early again to cover as much ground as possible in the next 12 hours. You beat the crowds to Willis Tower to enjoy beautiful city vistas from The Ledge, a glass balcony positioned on the 103rd story of the building. After being up high, you decide to make your way to the Navy Pier. This 3,300-foot-long pier over Lake Michigan encompasses more than 50 acres of gardens, parks, restaurants and shops, plus a variety of family attractions and exhibition space. Ranked as Chicago’s No. 1 tourist attraction and one of the Midwest’s most visited sites, Navy Pier has been open to the public since 1916 and is a must-see on any Chicago trip. It would also be downright wrong to travel here and not enjoy a slice — or entire pie — of the Chicago’s famous deep dish pizza. Fortunately, one of the most famous pizza establishments is around the corner from the hotel. Giordano’s does not take reservations and you know you will have to wait, but it will be worth it for one delicious dinner! Once you get a table, the ordering process is very easy. There is only one appropriate option to choose: the stuffed deep dish. (Giordano’s does offer starters, thin-crust and extra-thin crust pizzas, salads, sandwiches and other Italian favorites, too.) After dinner, you take a stroll along the Chicago River Canal and head back to the hotel to pack up and get ready to head home. What an action-packed weekend you’ve had! You know you’ll be back to Chicago soon to see even more of the gems this Midwestern city houses.