Bridgeport Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to S$1,300 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Where to stay in Bridgeport

Find the best Bridgeport areas and neighborhoods for the activities you enjoy most. Learn more about Bridgeport
A busy city street with tall buildings, a bus, and cars.

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.

Find hotels in Downtown Chicago
A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

Find hotels in Magnificent Mile
A river with yellow boats, a bridge, and tall buildings.

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

Find hotels in The Loop
A city street with a train passing overhead, cars, pedestrians, and a red brick building.

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.

Find hotels in River North
A wooden pavilion with a view of a city skyline and a body of water.

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.

Find hotels in Lincoln Park

Top hotels in Bridgeport

River Hotel

River Hotel

75 East Wacker Drive Chicago IL
S$283
25 Oct - 26 Oct
includes taxes & fees
River Hotel
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
S$243
25 Oct - 26 Oct
includes taxes & fees
8/10 Very good! (10,298 reviews)
"Very comfortable beds.very nice bathroom. AC could be better"

Reviewed on 30 Sept, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
S$272
27 Oct - 28 Oct
includes taxes & fees
8/10 Very good! (2,381 reviews)
"For the location & prestige, the grandeur was all in the external. The room was shabby, the carpet worn & marked (with bleach?) in several places, the amenities were severely lacking (front desk did not even have a sewing kit), staff were running on empty and ragged. Perhaps I had a lot of expectations ..."

Reviewed on 30 Sept, 2026

The Chicago Hotel Collection Ambassador Gold Coast
See all 4,662 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.

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 art galleries and fascinating museums in this vibrant area.
See properties

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.
See properties

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.
See properties

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.
See properties

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.
See properties

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.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

S$31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

S$51
per adult
92% of travellers recommend
Art Institute of Chicago
Flyover in Chicago

Flyover in Chicago

S$49
per adult
98% of travellers recommend
Flyover in Chicago
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.