Bridgeport Holidays
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- Plan, book, travel with confidence
- Better togetherSave up to NZ$2,400 when you book a flight and hotel together*
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Our guide on 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
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
Magnificent Mile
An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.
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.
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 of the city at Washington Station or Monroe Station (Blue Line).
Our pick of the best Bridgeport Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
NZ$213
8 Sept - 9 Sept
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
NZ$289
30 Aug - 31 Aug
includes taxes & fees
8/10 Very good! (1,981 reviews)
"There was mold on the curtains."
Reviewed on 11 Aug 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
NZ$458
11 Sept - 12 Sept
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 holiday package cost?
From as little as . 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 theatre 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 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 acclaimed art galleries 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 galleries and entertainment choices 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 fascinating museums and acclaimed theatre scene in this vibrant area.
Activities
Chicago: Navy Pier Centennial Wheel Ticket
NZ$42
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.