Bridgeport Vacations from $792

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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

Downtown Chicago
Save 100% on your flight
$792
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,631 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
$883
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Our first visit to Chicago, we chose this hotel based on price and reviews. It was amazing! Perfect location on the Magnificent Mile, we walked the city and saw all the sights. The BREAKFAST buffet included with stay is one of a kind! We enjoyed a nightcap at the rooftop bar amazed by the city skyline. The staff is so kind and helpful. HIGHLY RECOMMEND and we will absolutely stay there again as we are already planning our next trip to Chicago.

Reviewed on Aug 9, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
$2,857
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
Save 100% on your flight
$900
per person
Oct 21 - Oct 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
Save 100% on your flight
$1,800
per person
Sep 13 - Sep 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (512 reviews)

Where to stay in Bridgeport

Find the best Bridgeport areas and neighborhoods for the activities you enjoy most. Learn more about Bridgeport
A busy city street with tall buildings, a bus, and cars.

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
A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

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A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

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A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

Find hotels in River North
A nighttime cityscape with fireworks over a body of water, a Ferris wheel, and illuminated buildings.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more the city at Washington Station or Monroe Station (Blue Line).

Find hotels in Theatre District

Bridgeport Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$109 nightly
$130 total
Sep 8 - Sep 9
Total with taxes and fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$143 nightly
$170 total
Aug 30 - Aug 31
Total with taxes and fees
8/10 Very Good! (1,961 reviews)
"I was double charged. Still trying to get resolved!!"

Reviewed on Aug 9, 2026

The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
$216 nightly
$253 total
Aug 30 - Aug 31
Total with taxes and fees
8.4/10 Very Good! (2,379 reviews)
"Go place to stay if your traveling and have a connection next day. Also very safe! A bit expensive especially the valet parking"

Reviewed on Aug 9, 2026

Hilton Chicago O'Hare Airport
See all 4,589 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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Stay near popular Bridgeport attractions

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.
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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.
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Ramova Theatre

You can enjoy a show at Ramova Theatre on your trip to Chicago. Discover the area's entertainment venues and churches.
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Theatre on the Lake

You can make plans for a show at Theatre on the Lake during your stay in Chicago. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.
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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 acclaimed art scene and entertainment choices in this vibrant area.
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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 fascinating museums and acclaimed theater scene in this vibrant area.
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$27
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

$47
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
90% 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.