Sweet Home Chicago

Sweet Home Chicago

Sunday, May 9 – Friday, May 14

Explore the beautiful architecture, history, food, and culture that makes Chicago so special!

DAY 1- Fly from Boston to Chicago. We’ll check into our hotel, the Hilton Garden Inn, Chicago Downtown Riverwalk. You’ll have easy access to the Riverwalk, the Magnificent Mile, and Millenium Park.

DAY 2 – This morning, our local guide will take us on a 4-hour tour of Chicago’s highlights. See the city’s iconic Loop, lakefront, and Magnificent Mile, featuring landmarks such as the historic Water Tower on Michigan Avenue and the famed Chicago Theatre. You’ll get a chance to see celebrated public art including Cloud Gate (“The Bean”) and Crown Fountain, enjoy photo opportunities at Millennium Park, Buckingham Fountain, and Planetarium Point while discovering Chicago’s rich history, architecture, and pop culture. After our tour, you’ll have time for lunch on your own in Sterling Food Hall, a dynamic downtown dining destination offering a variety of local food concepts in a vibrant, community-focused setting. Then, explore Chicago’s blues music history with a tour of historic Chess Records recording studio used by the likes of Muddy Waters, Willie Dixon, Chuck Berry, Etta James, and numerous others. This afternoon, we’ll visit the BRAND-NEW Obama Presidential Center. Explore the 19.3-acre campus celebrating leadership, democracy, community engagement, and Chicago’s South Side. *Subject to availability, The museum is not scheduling guided tours for 2027 until fall 2026. Enjoy a delicious welcome dinner tonight. (B,D)

DAY 3 – Enjoy a free day with an included Big Bus Chicago hop-on/hop-off sightseeing pass to get you around the city with ease! Big Bus Chicago has many stops including Chicago Riverwalk, Millennium Park and the Art Institute, Museum Campus, Navy Pier, Magnificent Mile, John Hancock/360 Chicago. (B)

DAY 4 - Visit the Willis Tower (formerly Sears Tower) Skydeck to enjoy sweeping views from one of Chicago’s most iconic landmarks. While atop the SkyDeck, enjoy a classic Chicago Deep Dish Pizza lunch. We’ll take the Chicago’s Original Gangster Tour with our costumed Gangster Guide for an accurate account of the crimes and activities that were going on in Chicago during the 1920’s and ’30’s Prohibition Era. You will hear the exploits of Capone, Moran, Dillinger, and the rest of the boys on this unforgettable Chicago crime bus tour! Some sites you’ll see are the St.Valentine’s Day Massacre, the Biograph Theatre, and the Holy Name Cathedral.  We’ll visit the Richard H. Driehaus Museum, which explores the art, architecture, and design of the late 19th century to the present with a focus on the Gilded Age. The exhibits are presented in the restored Nickerson Mansion. During dinner, we’ll try to solve a murder mystery! Two mob families are being joined by a marriage, and with the two families merging, someone is bound to lose power, which means someone else will lose their life! It’s up to us to figure out who done it! (B,L,D)

DAY 5 - Step inside iconic Wrigley Field with behind-the-scenes access, Cubs history, and legendary ballpark views. Visit Chicago’s Navy Pier, a landmark lakefront destination with shops, restaurants, lake views, and entertainment. You’ll have time to explore on your own before we board a Shoreline Architecture River Cruise at Navy Pier for a 90-minute narrated cruise by Chicago’s famous city skyline. This revered architecture river cruise travels along all three branches of the Chicago River, offering a memorable view of the city’s world-famous buildings. Lunch will be on your own at Navy Pier. We’ll visit the world-renowned Art Institute of Chicago, one of the oldest and largest art museums in the country. Its collection includes masterpieces such as Georges Seurat's A Sunday on La Grande Jatte, Pablo Picasso's The Old Guitarist, Edward Hopper's Nighthawks, and Grant Wood's American Gothic. Enjoy free time afterwards - visit Millennium Park, the Chicago Cultural Center, or grab a cocktail at Cindy’s Rooftop, atop the Chicago Athletic Association Hotel. Tonight, enjoy dinner at The Berghoff Restaurant. (B, D)

DAY 6 – Bid farewell to Chicago and fly home to Boston. (B)

$ 2,759 per person, double occupancy (1 bed), $ 2,833 double occupancy (2 beds)

$ 3,490 single occupancy

Airfare TBA

Package Includes:

5 nights at the Hilton Garden Inn, Chicago Downtown Riverwalk

baggage handling

5 breakfasts, 1 lunch, 3 dinners

Obama Presidential Center*

Guided Tour of Chicago

Hop-On Hop-Off Bus Pass

Willis Tower Skydeck

Chicago Gangster Tour

Driehaus Museum

Navy Pier

Architecture River Tour

Chess Records tour

Art Institute of Chicago

Wrigley Field tour

Deluxe Motorcoach Transportation

Gratuities for tour escort, bus driver, and wait staff

Payment & Cancellation Policies:

Cash, personal checks & money orders accepted Visa & MasterCard payments accepted via phone.

Deposit of $100 per person is due upon booking Final Payment due 90 days out, refundable up to 90 days out