Bridgeport Holidays

Where to stay in Bridgeport

Find the best Bridgeport areas and neighborhoods for the activities you enjoy most. Learn more about Bridgeport
Downtown Chicago

Downtown Chicago

5 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

Top hotels in Bridgeport

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 S$210 per night from 29 Jun to 30 Jun
S$210
29 Jun - 30 Jun
includes taxes & fees
8/10 Very good! (10,187 reviews)
"Our room was spacious and clean. Everything works and soundproofing was great in a busy hotel. The only could make it better would be adding a door to the main bedroom and slightly larger TV (or just completely get rid of it)."

Reviewed on 25 Jun, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$227 per night from 7 Jul to 8 Jul
S$227
7 Jul - 8 Jul
includes taxes & fees
9/10 Wonderful! (4,456 reviews)
"Good location, bar and brunch were great. View from the pool and fitness centers was u real. Room was clean but sink faucet was loose and leaking and the bathroom door locks didn’t work well or would stick. Other than that it was nice."

Reviewed on 24 Jun, 2026

Hilton Chicago/Magnificent Mile Suites
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$313 per night from 5 Jul to 6 Jul
S$313
5 Jul - 6 Jul
includes taxes & fees
9.4/10 Exceptional! (4,529 reviews)
"Très bel hôtel bien situé dans un beau quartier ! Excellent rapport qualité-prix. Chambre un peu petite mais confortable! Très beau déjeuner de type buffet et très belle terrasse sur le toit mais menu limité."

Reviewed on 25 Jun, 2026

Hotel Riu Plaza Chicago
See all 4,768 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.

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$52
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

S$31
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.