Bridgeport Holidays

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Price found within the past 48 hours. Click for updated prices.
Sonesta Chicago O'Hare Airport Rosemont

Sonesta Chicago O'Hare Airport Rosemont

3 out of 5
O'Hare
per person
10 Oct - 13 Oct
found 17 hours ago
Return flight included
Fort Lauderdale (FLL) to Chicago (ORD)
8.6/10 Excellent! (1,537 reviews)
Sonesta was lovely. Easy check in. Nice room. Pillows not so great. Shuttle service was excellent as was all the staff!

Reviewed on 8 Aug, 2025

Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
O'Hare
per person
10 Oct - 13 Oct
found 17 hours ago
Return flight included
Fort Lauderdale (FLL) to Chicago (ORD)
8.8/10 Excellent! (1,001 reviews)
Amazing customer service.

Reviewed on 13 Aug, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
O'Hare
per person
10 Oct - 13 Oct
found 17 hours ago
Return flight included
Fort Lauderdale (FLL) to Chicago (ORD)
8.6/10 Excellent! (2,367 reviews)
Only 1 elevator was seemingly working so it took like 10 minutes every time you wanted to use one. People in the hallways were so noisy and slamming doors at all hours and the general look and appearance of the hotel seemed worse for wear. Definitely need to invest in some major renovations and upgrades.

Reviewed on 10 Aug, 2025

Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
O'Hare
per person
10 Oct - 13 Oct
found 17 hours ago
Return flight included
Fort Lauderdale (FLL) to Chicago (ORD)
8.8/10 Excellent! (2,250 reviews)
The property does have a nice modern aesthetic and is pleasant looking. The bathroom door is a sliding door and it was difficult to open as well as it has a very chincy lock that you can tell is damaged. The photos of the outdoor patio space definitely made it appear nicer than it actually is but was still at least pleasant. Check in staff seemed a little offputting and slightly pushy to get me going when I was asking questions. Breakfast is not complimentary and is quite expensive but there are nearby options to eat still. Overall seemed a little bit overpriced for the stay.

Reviewed on 11 Aug, 2025

Hilton Rosemont Chicago O'Hare

Hilton Rosemont Chicago O'Hare

3.5 out of 5
O'Hare
per person
10 Oct - 13 Oct
found 17 hours ago
Return flight included
Fort Lauderdale (FLL) to Chicago (ORD)
8.4/10 Very Good! (1,005 reviews)
Everything was perfect cool clean and respectful . Need more restaurants and fir Starbucks to close at 7 pm since there is only one restaurant to go too if don’t want to go out since we have no car

Reviewed on 11 Aug, 2025

Where to stay in Bridgeport

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

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$378 per night from 7 Sept to 8 Sept
S$378
7 Sept - 8 Sept
includes taxes & fees
7.8/10 Good! (8,960 reviews)
"Big rooms"

Reviewed on 12 Aug, 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$293 per night from 4 Sept to 5 Sept
S$293
4 Sept - 5 Sept
includes taxes & fees
8.4/10 Very Good! (1,842 reviews)
"This hotel is right in the heart of the city. You can walk to shows and attractions and the hotel is always welcoming."

Reviewed on 11 Aug, 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is S$216 per night from 2 Sept to 3 Sept
S$216
2 Sept - 3 Sept
includes taxes & fees
8.4/10 Very Good! (3,665 reviews)
"The staff was kind and helpful. The rooms and hotel itself were pretty clean. It's in a heavily populated area of a major US city - you're going to hear noises from outside at night, so just know that going into it(I've seen people complaining about it in reviews). I never felt unsafe walking around ..."

Reviewed on 11 Aug, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,673 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 S$681. 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

eSIM: Airalo United States Package

eSIM: Airalo United States Package

S$3
per traveller
eSIM: Airalo United States Package
Chicago: 2-Hour Kayak Rental from Bridgeport

Chicago: 2-Hour Kayak Rental from Bridgeport

S$62
per adult
Chicago: 2-Hour Kayak Rental from Bridgeport
River tour boat in Chicago

Architecture River Tour

S$53
per adult
96% of travellers recommend
Architecture River Tour
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.