Essex Vacations from $389
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Your Essex Vacation
When a break in the city is calling, answer it with a vacation package to Essex. The neighborhood of Magnificent Mile, which is great for cafes, shopping and history, makes an excellent base for your adventures. Every trip to Essex needs a well-planned itinerary. Fill yours with leading attractions like University of Chicago, Chicago Museum of Science and Industry and Guaranteed Rate Field. No matter your travel plans or budget, organizing a tailored Essex vacation is a walk in the park with Expedia.
The Latest Essex Vacation Packages
Chicago Lake Shore Hotel
Reviewed on Sep 22, 2026
Level Chicago – Old Town
Reviewed on Sep 19, 2026
Stay One Chicago
Reviewed on Sep 20, 2026
Where to stay in Essex
Downtown Chicago
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
Essex Hotel Deals
River Hotel
"I had a fantastic stay! The location was perfect—right next to the Hello Kitty Café and directly across from the Trump Hotel, which made for a beautiful view from my room. Everything was clean, comfortable, and overall a great experience. The only downside was that only one elevator was operating ..."
Reviewed on Sep 22, 2026
Congress Plaza Hotel
"I’ve stayed here for years. Every riot"
Reviewed on Sep 22, 2026
The Chicago Hotel Collection Ambassador Gold Coast
Things to do
