Bridgeport Vacations from $694

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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.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,052, price is now $694 per person
$694
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
Thank you to Javon who was super helpful in our check in . The staff was so nice and accommodating. Additional linens were delivered in less than 5 minutes and then even extended our check out to 1pm. I will definitely be back when I’m in Chicago to try to catch fireworks. Our corner room was outstanding and breathtaking

Reviewed on May 3, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,514, price is now $846 per person
$846
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (462 reviews)
The rooms were very clean!

Reviewed on May 4, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,464, price is now $929 per person
$929
per person
Jul 22 - Jul 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (468 reviews)
Love the amenities. Great location too

Reviewed on May 3, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,531, price is now $1,007 per person
$1,007
per person
Jun 26 - Jun 29
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (973 reviews)
Rooms were cleaned I liked how secure the hotel was.

Reviewed on Apr 29, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,703, price is now $1,152 per person
$1,152
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
The staff was very welcoming and the rooms were super clean & well maintained. The location is also very convenient, quiet but close and walking distance to the river and the amazing restaurants. Will definitely revisit the Penninsula soon.

Reviewed on May 2, 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

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.

Find hotels in Downtown Chicago

Bridgeport Hotel Deals

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
$125 nightly
The price is $148 total per night from May 25 to May 26
$148 total
May 25 - May 26
Total with taxes and fees
8.2/10 Very Good! (2,683 reviews)
Friendly staff. Good location

Reviewed on May 5, 2026

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$135 nightly
The price is $161 total per night from May 26 to May 27
$161 total
May 26 - May 27
Total with taxes and fees
8.8/10 Excellent! (5,168 reviews)
Great

Reviewed on May 6, 2026

River Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
$151 nightly
The price is $180 total per night from May 27 to May 28
$180 total
May 27 - May 28
Total with taxes and fees
9.4/10 Exceptional! (4,070 reviews)
Very nice and clean hotel. Wonderful break fast buffet with good selection of food.

Reviewed on May 6, 2026

Hotel Riu Plaza Chicago
See all 4,753 properties in Bridgeport
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

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 fascinating museums and acclaimed theater scene in this vibrant area.

Bridgeport Art Center

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.

Zhou B Art Center

Palmisano Park

Palmisano Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the entertainment choices and acclaimed theater scene in this vibrant area.

Palmisano Park

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$27
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

$44
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

$38
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.