Bridgeport Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
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Top Holiday Package Deals in Bridgeport
Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
CA $1,013
per person
Nov 10 - Nov 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,654 reviews)
The hotel was clean. The staff was amazing. The location is also great. I love being right on the water. Perfect for a stroll outside on the boardwalk.
Reviewed on Aug 29, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,727
per person
Oct 9 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Room was ok, didn’t get the view I requested.
Some of the reception people was rude. Breakfast was adequate. No omellete bar,
Reviewed on Aug 29, 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
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.
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.
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.
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.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
Bridgeport Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $148
CA $176 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very good! (10,203 reviews)
"The hotel is old and needs a renovation. Carpets are worn and dirty, and you can tell that it hasn't had a refresh in 30+ years. However, we left important medicine behind and we coordinated with them to have it sent to us at our next stop...they were VERY helpful in this regard so despite a negative ..."
Reviewed on Aug 29, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $199
CA $236 total
Aug 31 - Sep 1
includes taxes & fees
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
CA $324
CA $381 total
Sep 18 - Sep 19
includes taxes & fees
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.
Frequently asked questions
How much does a Bridgeport vacation package cost?
From as little as CA $1,013. 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.
Stay near popular Bridgeport attractions
Bridgeport Art Center
Enjoy a stop at Bridgeport Art Center, an entertaining place to visit in Chicago. Experience the acclaimed theater scene and fascinating museums in this vibrant area.
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.
Ramova Theatre
You can enjoy a show at Ramova Theatre on your trip to Chicago. Discover the area's entertainment venues and churches.
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.
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.
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.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.