Bridgeport Vacation Packages

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Top Holiday Package Deals in Bridgeport

Prices and availability subject to change. Additional terms may apply.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 18 - Jul. 21
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The staff were welcoming, courteous, and friendly. The location was perfect and room was beautiful and clean!

Reviewed on Apr. 14, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 8 - Jul. 11
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,152 reviews)
Amazing. Definitely coming back!

Reviewed on Apr. 20, 2024

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul. 18 - Jul. 21
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,007 reviews)
The staff are thoughtful and provide the best service. While I was there, I was already planning to come back and stay there again!

Reviewed on Apr. 24, 2024

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
per person
Jul. 8 - Jul. 11
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (95 reviews)
Outstanding service and facility.

Reviewed on Jan. 10, 2024

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jun. 6 - Jun. 9
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,009 reviews)
By far my favorite place to stay in Chicago! Beautiful location, clean and staff is amazing! Loved our view, can't wait to visit again

Reviewed on Apr. 25, 2024

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

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Grant Park and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotel + flight trips 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
The price is CA $166 per night from Apr. 28 to Apr. 29
CA $166
CA $195 total
includes taxes & fees
Apr 28 - Apr 29
7.6/10 Good! (6,588 reviews)
"A great older hotel. Very happy with my stay here."

Reviewed on Apr. 23, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $180 per night from Apr. 28 to Apr. 29
CA $180
CA $212 total
includes taxes & fees
Apr 28 - Apr 29
8.6/10 Excellent! (2,686 reviews)
"Wonderful stay in the best part of town"

Reviewed on Apr. 24, 2024

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $232 per night from Apr. 28 to Apr. 29
CA $232
CA $273 total
includes taxes & fees
Apr 28 - Apr 29
8.2/10 Very Good! (1,853 reviews)
"When we booked with Hotels it said our room would have a balcony and it didnt. It also said it had roof top outdoor sitting and it was closed also. If it had said it wasn't opened to sit up there or the balconies we couldnt use i would not of booked with that hotel."

Reviewed on Apr. 22, 2024

Eurostars Magnificent Mile
See all 4,183 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Bridgeport vacation package cost?
From as little as CA $783. Yes, you read that right. Our Bridgeport packages are an easy way to make your budget last longer. Bundle your favorite flights, hotels and rental car and get out and see this destination your way.
How do I get a cheap travel package to Bridgeport?
One of the simplest ways to save dollars (and time) is to bundle your bookings with Expedia. Flights, rental cars, hotels and activities — we’ve got it all. Choose the combination that best fits you and watch your savings stack up. We know a package deal is never one-size-fits-all. That’s why we offer over 550 airlines and 1,000,000 properties globally, which lets you customize your Bridgeport getaway.
Where should I stay in Bridgeport?
Make sightseeing easier by staying someplace just around the corner from Bridgeport’s fantastic attractions. University of Chicago and Chicago Museum of Science and Industry are two visitor favorites.
How far in advance should I book my Bridgeport vacation?
Savvy travelers will likely want to reserve their seats as early as possible. You can normally start comparing international airfares on Expedia up to 12 months before your flight. If you’re booking last minute, don’t despair. Cheap prices sometimes occur in the last weeks before departure dates.
What does an Expedia Bridgeport travel package include?
From hotels and flights to rental cars, Expedia can help you create a Bridgeport package that’s ideal for you. Vacationing for a few weeks? Give some thought to a flight, rental car and hotel bundle. If you can only manage a quick getaway, a flight and hotel deal could be what you’re after. Tours and activities can be added once you’ve made your booking. Our travel packages make it a breeze to save and plan.
What should I know before booking a Bridgeport travel package?
A package can be easier on the bank balance than individually booking all you need for your escape. For example, combine your hotels, flights and rental cars and score big savings. Whatever type of vacation you have in mind, you’re bound to find a package to suit your budget.
Can I choose my airline with a Bridgeport Expedia vacation package?
Expedia has access to more than 550 airline partners globally, so you definitely can. Simply pick the carrier you want and craft the perfect Bridgeport trip.
If I'm not able to travel, can I cancel my Bridgeport vacation package?
It is possible to cancel your Bridgeport booking if your plans have changed. Whether you’ll incur a penalty or not depends on your hotel, airline or car rental company. It may be possible to change or cancel for free if you booked in the last 24 hours. Head to our Customer Service Portal to learn more.

Discover the most popular places to visit in Bridgeport

Image for Bridgeport Art Center

Bridgeport Art Center

You can enjoy some culture when you stop by Bridgeport Art Center in Chicago. Experience the acclaimed theater scene and fascinating museums in this vibrant area.

Bridgeport Art Center
Image for Zhou B Art Center

Zhou B Art Center

You can enjoy some culture when you stop by Zhou B Art Center in Chicago. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.

Zhou B Art Center
Image for Bubbly Creek

Bubbly Creek

Commune with nature and explore the great outdoors at Bubbly Creek during your travels in Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.

Bubbly Creek

Things to do

Image for Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

CA $73
Per adult
92% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
Image for Chicago Pizza Tour

Chicago Pizza Tour

CA $102
Per adult
100% of travellers recommend
Chicago Pizza Tour
Image for Chicago Museum of Contemporary Art: General Admission Ticket

Chicago Museum of Contemporary Art: General Admission Ticket

CA $30
Per adult
90% of travellers recommend
Chicago Museum of Contemporary Art: General Admission Ticket
See all activities in Chicago

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.