Bridgeport Vacations from $249

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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.
Hampton Inn & Suites Chicago Medical District UIC

Hampton Inn & Suites Chicago Medical District UIC

2.5 out of 5
Near West Side
Save 100% on your flight
Price was $430, price is now $249 per person
$249
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (281 reviews)
From the time we came through the front door we were greeted with a smile can’t remember their names but very good customer service rooms were great housekeeping gave me what I needed everyone greeted us every time we enter the lobby area Mike an Ashley checked us out with smiles they took time and ask how was our stay very knowledgeable about the billing also breakfast was excellent everything and everyone was great Thank you Jacqueline Robinson

Reviewed on Oct 21, 2025

The Westin Michigan Avenue Chicago

The Westin Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was $840, price is now $345 per person
$345
per person
Nov 24 - Nov 27
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,070 reviews)
Hotel in great location, would stay again

Reviewed on Oct 19, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $835, price is now $445 per person
$445
per person
Dec 30 - Jan 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,248 reviews)
We really like The Emily Hotel Chicago. We've stayed a few times this year because the location is very near many great restaurants and bars. The hotel itself has really good dining and lounge options. The staff treats us very well and the rooms and beds are clean and comfortable. A great hotel in a really fun part of town!

Reviewed on Oct 22, 2025

Art Villa

Art Villa

5 out of 5
West Town
Save 100% on your flight
Price was $1,108, price is now $610 per person
$610
per person
Jan 1 - Jan 4
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
10/10 Exceptional! (2 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $883, price is now $507 per person
$507
per person
Nov 27 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,602 reviews)
Everything was perfect. Will stay at Riu Plaza again.

Reviewed on Oct 24, 2025

Where to stay in Bridgeport

Find the best Bridgeport areas and neighborhoods for the activities you enjoy most. Learn more about Bridgeport
Downtown Chicago showing a city

Downtown Chicago

5 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

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $136 total per night from Nov 24 to Nov 25
$136 total
Nov 24 - Nov 25
Total with taxes and fees
7.8/10 Good! (9,567 reviews)
LOVED the room and the view was spectacular! The location could not have been any more convenient. Lobby was beautiful. Our room had a separate living room with bay windows looking out over Lake Michigan and the city. The bedroom was fantastic with a comfortable bed and pillows. We slept so well. ...

Reviewed on Oct 24, 2025

Congress Plaza Hotel
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
Fully refundable
$139 nightly
The price is $163 total per night from Nov 23 to Nov 24
$163 total
Nov 23 - Nov 24
Total with taxes and fees
8.8/10 Excellent! (1,948 reviews)
We didn’t know what to expect from a Holiday Inn in a tower and were pleasantly surprised. The building — hotel actually starts on the 15th floor — is like new and was very clean. The staff was universally friendly. The lobby floor has a grab-and-go food option available 24 hours and a nontraditional ...

Reviewed on Oct 20, 2025

Holiday Inn Chicago Dwtn - The Mart by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $131 total per night from Nov 16 to Nov 17
$131 total
Nov 16 - Nov 17
Total with taxes and fees
8.8/10 Excellent! (3,135 reviews)
Great

Reviewed on Oct 23, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,664 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.
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Discover the most popular places to visit in Bridgeport

Bridgeport Art Center

You can spend time studying the exhibits at Bridgeport Art Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

Bridgeport Art Center

Zhou B Art Center

You can spend time studying the exhibits at Zhou B Art Center during your trip to Chicago. Experience the entertainment choices and 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

River tour boat in Chicago

Architecture River Tour

$49
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

$44
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.