Bridgeport Vacation Packages
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Top Holiday Package Deals in Bridgeport
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
per person
Aug. 23 - Aug. 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,166 reviews)
We like staying at this property because it is convenient to many shopping and restaurant venues within a couple blocks.
The only thing that we didn’t like is that sometimes the unhoused individuals would come into the Ground floor entrance and beg for money. The security desk is not manned at times.
Other than that, the property is well kept and the staff is incredible! This was our second time staying here and we will stay again.
Reviewed on Jun. 17, 2024
W Chicago - Lakeshore
Downtown Chicago
Save 100% on your flight
per person
Aug. 24 - Aug. 31
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
8.2/10 Very Good! (1,006 reviews)
Good stay at the W, staff was very nice and organized.
Would stay there again for sure.
Reviewed on Jun. 17, 2024
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug. 22 - Aug. 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,230 reviews)
Location is amazing, super friendly staff. Will definitely be back soon
Reviewed on Jun. 17, 2024
Where to stay in Bridgeport
Find the best Bridgeport areas and neighborhoods for the activities you enjoy most. Learn more about Bridgeport
Downtown Chicago
4 out of top 10 points of interest in this area
Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Grant Park and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
Bridgeport Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $187 per night from Jul. 1 to Jul. 2
CA $187
CA $219 total
includes taxes & fees
Jul 1 - Jul 2
7.6/10 Good! (7,017 reviews)
"Lovely stay right in the middle of it all."
Reviewed on Jun. 17, 2024
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $249 per night from Jul. 1 to Jul. 2
CA $249
CA $293 total
includes taxes & fees
Jul 1 - Jul 2
8/10 Very Good! (2,400 reviews)
Great stay loved it
"Love staying at the embassy suits. Breakfast as well as there social hour"
Reviewed on Jun. 18, 2024
River Hotel
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $199 per night from Jul. 1 to Jul. 2
CA $199
CA $234 total
includes taxes & fees
Jul 1 - Jul 2
8.6/10 Excellent! (2,952 reviews)
"This was such a conveniently located hotel. We were able to walk to so many places. The guy that checked us in was super friendly and set the tone for a really nice stay. I also really appreciated to cold filtered water stations all over to refill our water bottles. I would definitely stay here ..."
Reviewed on Jun. 16, 2024
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Explore other types of vacation packages
Frequently asked questions
Discover the most popular places to visit in Bridgeport
Bridgeport Art Center
You can enjoy some culture when you stop by Bridgeport Art Center in Chicago. Experience the entertainment choices and fascinating museums in this vibrant area.
Zhou B Art Center
You can enjoy some culture when you stop by Zhou B Art Center in Chicago. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.
Bubbly Creek
Commune with nature and explore the great outdoors at Bubbly Creek during your travels in Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.
Things to do
Odyssey Lake Michigan Premier Dinner Cruise
CA $255
Per adult
76% of travellers recommend
Chicago: City Minibus Tour with Optional Architecture Cruise
CA $64
Per adult
98% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.