Bridgeport Vacations from $267

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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.
Holiday Inn Chicago - Schaumburg by IHG

Holiday Inn Chicago - Schaumburg by IHG

3.5 out of 5
Price was $432, price is now $267 per person
$267
per person
Apr 9 - Apr 13
just found
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.2/10 Very Good! (999 reviews)
Staff was very courteous however the hotel needs to be updated. One little tiny bar of soap in the room was rather skimpy.

Reviewed on Jan 11, 2026

La Banque Hotel

La Banque Hotel

4 out of 5
Price was $1,047, price is now $540 per person
$540
per person
Apr 22 - Apr 28
found 10 hours ago
Roundtrip flight included
Houston (HOU) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.

Reviewed on Jan 26, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $513, price is now $292 per person
$292
per person
Mar 6 - Mar 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Beautiful room, great location. Will definitely stay there again.

Reviewed on Jan 28, 2026

Stay One Chicago

Stay One Chicago

2 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,941, price is now $1,250 per person
$1,250
per person
Apr 22 - Apr 28
found 13 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
No reviews
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $602, price is now $395 per person
$395
per person
Apr 10 - Apr 13
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Property was clean, welcoming, pet friendly

Reviewed on Jan 18, 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 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
$91 nightly
The price is $107 total per night from Jan 30 to Jan 31
$107 total
Jan 30 - Jan 31
Total with taxes and fees
8/10 Very Good! (9,832 reviews)
Yes perfectly clean

Reviewed on Jan 24, 2026

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $125 total per night from Feb 8 to Feb 9
$125 total
Feb 8 - Feb 9
Total with taxes and fees
8.4/10 Very Good! (5,617 reviews)
Friendly desk staff, clean room. Fridge didn't have temp adjuster and contents froze, bottles broke.

Reviewed on Jan 28, 2026

Embassy Suites by Hilton Chicago Downtown River North
DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
300 E Ohio St Chicago IL
Fully refundableReserve now, pay when you stay
$85 nightly
The price is $100 total per night from Feb 5 to Feb 6
$100 total
Feb 5 - Feb 6
Total with taxes and fees
8.6/10 Excellent! (2,264 reviews)
Great

Reviewed on Jan 27, 2026

DoubleTree by Hilton Chicago - Magnificent Mile
See all 4,944 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

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 fascinating museums.

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 fascinating museums and entertainment choices in this vibrant area.

Zhou B Art Center

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 entertainment choices and acclaimed theater scene in this vibrant area.

Stephen A. Douglas Tomb and Memorial

Things to do

Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$61
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

$25
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Chicago Blackhawks Ice Hockey Game at United Center

Chicago Blackhawks Ice Hockey Game at United Center

$67
per adult
Chicago Blackhawks Ice Hockey Game at United Center
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.