Bridgeport Trip
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Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
₹98,955
per person
30 Oct - 2 Nov
found 10 hours ago
Return flight included
Toronto (YYZ) to Chicago (ORD)
9.6/10 Exceptional! (1,995 reviews)
One of the best hotels in the city, I would do it over again in the blink of an eye
Reviewed on 14 Sept 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.
Magnificent Mile
A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Top hotels in Bridgeport
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
₹14,699
₹17,475 total
27 Sept - 28 Sept
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
₹15,382
₹18,288 total
28 Sept - 29 Sept
includes taxes & fees
8/10 Very good! (2,239 reviews)
"Everything was fine except that the mini-refrigerator in our room did not work."
Reviewed on 14 Sept 2026
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
₹16,318
₹19,401 total
27 Sept - 28 Sept
includes taxes & fees
8/10 Very good! (10,248 reviews)
"Everything was really nice except the A/C unit wasn't powerful enough to cool the room. When we checked in the curtains were open and the room was extremely warm and never fully cooled. Luckily we had a travel fan that made the room bearable. All other aspects of our stay were great the staff were ..."
Reviewed on 14 Sept 2026
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 holiday package cost?
From as little as ₹46,488. Yes, you read that right. Our Bridgeport packages are an easy way to make your budget last longer. Bundle your favourite 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 favourites.
How far in advance should I book my Bridgeport holiday?
Savvy travellers 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. Holidaying 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 holiday you have in mind, you're bound to find a package to suit your budget.
Can I choose my airline with a Bridgeport Expedia holiday 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 holiday 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 art galleries 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 galleries in this vibrant area.
Ramova Theatre
You can get tickets for a performance at Ramova Theatre on your trip to Chicago. Discover the area's entertainment choices and churches.
Theatre on the Lake
You can make plans for a show at Theatre on the Lake on your trip to Chicago. Stroll along the lakeside or experience the fascinating museums 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 entertainment choices and acclaimed theatre scene in this vibrant area.
Stephen A. Douglas Tomb and Memorial
Find out about the history of Chicago when you spend time at Stephen A. Douglas Tomb and Memorial. Experience the entertainment choices and fascinating museums in this vibrant area.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.