Bridgeport Vacations from $720
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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
Hotel Riu Plaza Chicago
Reviewed on Mar 20, 2026
Level Chicago Fulton Market
Reviewed on Mar 14, 2026
Level Chicago – Old Town
Reviewed on Mar 17, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Reviewed on Mar 20, 2026
Thompson Chicago, by Hyatt
Reviewed on Mar 17, 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.
Bridgeport Hotel Deals
Congress Plaza Hotel
Everything was clean and the staff were very nice!
Reviewed on Mar 20, 2026
Hotel Riu Plaza Chicago
The breakfast was incredibly delicious. The hotel in general is a 10 out of 10.
Reviewed on Mar 20, 2026
Embassy Suites by Hilton Chicago Downtown River North
Hotel is conveniently located, clean and rooms were spacious. Evening reception and breakfast selections are fantastic. The only downside was the pool area is small with limited seating but the kiddos still enjoyed. Staff was very professional and helpful. Would stay again.
Reviewed on Mar 20, 2026
Discover the most popular places to visit in Bridgeport
Bridgeport Art Center
Enjoy a stop at Bridgeport Art Center, an entertaining place to visit in Chicago. Experience the acclaimed theater scene and fascinating museums in this vibrant area.
Zhou B Art Center
Enjoy a stop at Zhou B Art Center, an entertaining place to visit in Chicago. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.
Stephen A. Douglas Tomb and Memorial
Find out about the history of Chicago with a stop at Stephen A. Douglas Tomb and Memorial. Experience the entertainment choices and acclaimed art scene in this vibrant area.
Things to do
