Bridgeport Vacations from ₩1,240,666

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  • Better together

    Save up to ₩234,741 when you book a flight and hotel together*

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

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The Latest Bridgeport Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was ₩1,611,162, price is now ₩1,240,666 per person
₩1,240,666
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Cedar Rapids (CID) to Chicago (ORD)
9.4/10 Exceptional! (2,229 reviews)
The view really makes this hotel worth it! The bench in my room was a bit worn but other than that nice hotel and great stay

Reviewed on Dec 31, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ₩1,925,886, price is now ₩1,291,332 per person
₩1,291,332
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Cedar Rapids (CID) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Jasmine was courteous and friendly, made our check in process smooth. Clean rooms and the breakfast was amazing. I definitely recommend staying here.

Reviewed on Dec 31, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was ₩2,479,682, price is now ₩1,699,954 per person
₩1,699,954
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Cedar Rapids (CID) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
It was like a Ritz Carlton like experience without the Ritz Carlton price tag.

Reviewed on Dec 31, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was ₩1,888,250, price is now ₩1,387,130 per person
₩1,387,130
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Cedar Rapids (CID) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Staff was friendly did amazing job with checking us in

Reviewed on Dec 25, 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was ₩1,900,232, price is now ₩1,447,446 per person
₩1,447,446
per person
Mar 12 - Mar 16
found 1 day ago
Roundtrip flight included
Cedar Rapids (CID) to Chicago (ORD)
9.4/10 Exceptional! (3,392 reviews)
Location, location, location... and if you ad a great breakfast dinner you're all set to enjoy Chicago.

Reviewed on Dec 31, 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 showing 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

Bridgeport Hotel Deals

Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is ₩198,125 per night from Jan 22 to Jan 23
₩198,125
₩274,540 total
Jan 22 - Jan 23, 2026
includes taxes & fees
8.4/10 Very Good! (2,445 reviews)
Best option for us while attending an event at McCormick place, with ability to park in public parking that is cheaper than the hotel parking!

Reviewed on Dec 30, 2025

Hilton Chicago
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 ₩128,674 per night from Jan 6 to Jan 7
₩128,674
₩151,049 total
Jan 6 - Jan 7, 2026
includes taxes & fees
8.8/10 Excellent! (3,613 reviews)
Clean room , great location.

Reviewed on Dec 30, 2025

Hilton Chicago/Magnificent Mile Suites
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 ₩203,987 per night from Jan 29 to Jan 30
₩203,987
₩275,203 total
Jan 29 - Jan 30, 2026
includes taxes & fees
8.4/10 Very Good! (2,195 reviews)
Our stay was absolutely perfect. The room was clean. The staff was amazing! The decorations were festive and the pool was spotless warm and very very family friendly!!

Reviewed on Dec 29, 2025

Palmer House a Hilton Hotel
See all 4,827 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 vacation package cost?
From as little as ₩1,240,666. Yes, you read that right. Our Bridgeport packages are an easy way to make your budget last longer. Bundle your favorite 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 favorites.
How far in advance should I book my Bridgeport vacation?
Savvy travelers 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. Vacationing 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 vacation you have in mind, you're bound to find a package to suit your budget.
Can I choose my airline with a Bridgeport Expedia vacation 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 vacation 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.

Discover the most popular places to visit in Bridgeport

Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Millennium Park featuring a city, modern architecture and fall colors

Millennium Park

4.5/5(7,198 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park
Grant Park showing a garden and night scenes

Grant Park

4.5/5(3,318 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.