Compare All-Inclusive Resorts in Chicago in 2026

The scent of deep-dish pizza hits you like a warm high-five, powerful yet life-affirming. You can imagine the perfectly melted cheese blanketed by a savory lake of marinara before you see it. And when the doughy triangle passes your lips, you’re reminded of childhood sleepovers spent ordering pizza and telling secrets. But no pie you’ve ever had before can contend with the deep-dish creations of Chicago. In Chi-Town, your pizza-loving heart has found its home. And when you bite into an epic hot dog, your love for ballpark fare reaches new heights.

Welcome to the jewel of Illinois, a city on Lake Michigan that marries culinary masterpieces (and not just pizza) with art, culture, and a healthy dose of sports fanaticism. Within steps of your Chicago all-inclusive hotel you’ll find everything from elegant restaurants and upscale shopping to the Museum of Science and Industry.

Where is the best area to stay in downtown Chicago?

Many of the best all-inclusive hotels in Chicago are in The Loop, and that’s no accident. The Loop is named for the train tracks that surround it, and it’s not only situated near transportation—some of the most famous attractions are here, too near many of the great hotels such as Homewood Suites downtown. Spot your reflection in the Cloud Gate sculpture, a giant metallic bean that draws plenty of attention and reminds you how small your place is in the universe. Meanwhile, Millennium Park is just steps from most hotels in The Loop and you won’t find a better place to eat and shop while you’re visiting Chicago. Nearby in South Loop, your hotel puts you within walking distance of places like the Adler Planetarium and 12th Street Beach.

How do I get to Navy Pier from Union Station?

The easiest way to get from Union Station to Navy Pier is via the CTA bus system. Just hop on CTA #124, and you will be delivered right to the pier in under 30 minutes when traffic is light. You can also drive the 3.5-mile distance in your rental car if you want to have a bit more freedom in your itinerary. Between May and September, you can also take the Shoreline water taxi service between Union Station and the Navy Pier via the Chicago River. Once you arrive at your destination, a beer garden, Ferris wheel, and high-speed boat ride await. Sip away your worries at Margaritaville, and you might swear you were on island time, right here in the middle of the heartland.

From the moment you arrive in Chicago, the lively spirit of the city will envelop you. Stand before its towering skyscrapers and behold its magic bean. Let yourself be taken away by its warmth and the shimmering water of Lake Michigan during summer months. Always book all-inclusive hotels in Chicago, including the Silversmith Hotel Chicago Downtown, right here on Travelocity. When you find a great deal on your hotel room, you’re already wandering wisely.