Bridgeport Vacations from $301
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Your Bridgeport Vacation
Take the stress out of travel planning with a Bridgeport vacation package. With all the details locked in before you head off, all you have to do is enjoy this riverside neighborhood's cafes, dining and history. Your trip to Bridgeport wouldn't be complete without seeing major attractions nearby such as Guaranteed Rate Field, Illinois Institute of Technology and Bridgeport Art Center. Don't just think about it — take action! Book your ultimate Bridgeport vacation with Expedia and experience travel your way.
The Latest Bridgeport Vacation Packages
Chicago Lake Shore Hotel
Reviewed on Sep 15, 2026
Where to stay in Bridgeport
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.
Bridgeport Hotel Deals
River Hotel
"Location was perfect. Staff were nice."
Reviewed on Sep 16, 2026
The Chicago Hotel Collection Ambassador Gold Coast
Congress Plaza Hotel
"The Congress Plaza Hotel is old, but affordable. If you're not after a high level of comfort and just need a clean and conveniently located place to sleep that is probably more affordable than anywhere else in downtown Chicago, then this hotel should do nicely for you."
Reviewed on Sep 16, 2026
Stay near popular Bridgeport attractions
Bridgeport Art Center
Zhou B Art Center
Ramova Theatre
Theatre on the Lake
Palmisano Park
Stephen A. Douglas Tomb and Memorial
Things to do
