Bridgeport Vacations from $286
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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
Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago
Downtown Chicago
Price was $402, price is now $286 per person
$286
per person
Jan 22 - Jan 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything.
Reviewed on Nov 3, 2026
Pendry Chicago
Downtown Chicago
Price was $704, price is now $483 per person
$483
per person
Jan 28 - Jan 31
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.
Reviewed on Nov 8, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $571, price is now $394 per person
$394
per person
Jan 14 - Jan 17
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,555 reviews)
The staff were more ghan helpful even when checking in after midnight
The room was very spacious and clean
The breakfast selection catered for everyone with good quality food foe everyone
Had a wonderful stay, could not find a fault
Thank you for your hospitality during our stsy
Reviewed on Nov 9, 2026
Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $569, price is now $397 per person
$397
per person
Jan 15 - Jan 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,962 reviews)
Good but the condition of the room wasn’t the best.
Reviewed on Nov 8, 2026
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
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
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $126 total per night from Nov 22 to Nov 23
$126 total
Nov 22 - Nov 23
Total with taxes and fees
8/10 Very Good! (10,139 reviews)
"This was the perfect spot for our Chicago adventure. Easy access to parks, shopping, dining, transportation options, and beautiful views, I was also grateful to be able to park my car safely and easily. Rooms and facilities were clean and comfortable!"
Reviewed on Nov 9, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $138 total per night from Nov 11 to Nov 12
$138 total
Nov 11 - Nov 12
Total with taxes and fees
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$106 nightly
The price is $126 total per night from Dec 10 to Dec 11
$126 total
Dec 10 - Dec 11
Total with taxes and fees
8.8/10 Excellent! (5,599 reviews)
"When we arrived the sheets were dirty so we had to request them to be changed. The property can use an upgrade. The rooms are extremely small so this is not a good option if you like to be in the room. Fortunately we were out and about the whole trip. I love the convenient location."
Reviewed on Nov 8, 2026
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.
Stay near popular Bridgeport attractions
Things to do
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Chicago's Navy Pier Centennial Wheel Ticket
$24
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.