Bridgeport Vacations from ￥54,896

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    Save up to ￥45,448 when you book a flight and hotel together*

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The Latest Bridgeport Vacation Packages

Price found within the past 48 hours. Click for updated prices.
OYO Hotel Portage I-94

OYO Hotel Portage I-94

2 out of 5
Price was ￥60,657, price is now ￥54,896 per person
￥54,896
per person
Jan 6 - Jan 8
found 2 hours ago
Roundtrip flight included
Omaha (OMA) to Chicago (ORD)
6.4/10 (748 reviews)
Older rooms but serviced the purpose.

Reviewed on Nov 5, 2025

Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
East Hazel Crest
Price was ￥78,869, price is now ￥69,802 per person
￥69,802
per person
Jan 6 - Jan 8
found 2 hours ago
Roundtrip flight included
Omaha (OMA) to Chicago (MDW)
18.8/10 Exceptional! (155 reviews)
Great staff! Clean rooms!

Reviewed on Nov 15, 2025

Motel Edgebrook Chicago North Shore by OYO

Motel Edgebrook Chicago North Shore by OYO

2 out of 5
Forest Glen
Price was ￥65,596, price is now ￥60,298 per person
￥60,298
per person
Jan 6 - Jan 8
found 1 day ago
Roundtrip flight included
Omaha (OMA) to Chicago (ORD)
6.2/10 (353 reviews)
For a cheap hotel, it’s fine as it has the basic necessities a hotel needs - however, it was slightly dirty, microwave didn’t work, and no plugs. The side lights on the nightstands didn’t work and the room was hot (no temperature regulation). For the price it’s fair

Reviewed on Nov 2, 2025

Wyndham Garden Schaumburg Chicago Northwest

Wyndham Garden Schaumburg Chicago Northwest

3 out of 5
Price was ￥62,447, price is now ￥57,657 per person
￥57,657
per person
Jan 6 - Jan 8
found 1 day ago
Roundtrip flight included
Omaha (OMA) to Chicago (ORD)
13.2/10 Exceptional! (1,001 reviews)
It was quiet and affort

Reviewed on Nov 14, 2025

WorldMark Galena

WorldMark Galena

2.5 out of 5
Price was ￥195,954, price is now ￥182,346 per person
￥182,346
per person
Feb 3 - Feb 6
found 5 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (CHI)
17.6/10 Exceptional! (238 reviews)
Rooms were cozy and beautiful the two bedroom kitchenettes were wonderful and spacious for my family. The one bed room was nice a little small to cook but nice and comfy.

Reviewed on Oct 19, 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

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

Bridgeport Hotel Deals

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥15,081 per night from Nov 23 to Nov 24
￥15,081
￥17,704 total
Nov 23 - Nov 24
includes taxes & fees
8.4/10 Very Good! (5,235 reviews)
Clean room; kind and courteous staff; excellent breakfast and happy hour included

Reviewed on Nov 10, 2025

Embassy Suites by Hilton Chicago Downtown River North
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 ￥15,081 per night from Dec 7 to Dec 8
￥15,081
￥17,704 total
Dec 7 - Dec 8
includes taxes & fees
8.8/10 Excellent! (3,290 reviews)
I loved that everything was in walking distance. It was very clean. The hospitality service was excellent! Very kind and friendly!

Reviewed on Nov 14, 2025

Hilton Chicago/Magnificent Mile Suites
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥17,602 per night from Nov 16 to Nov 17
￥17,602
￥20,664 total
Nov 16 - Nov 17
includes taxes & fees
9.2/10 Wonderful! (4,021 reviews)
Yes 10/10 definitely will be back soon

Reviewed on Nov 11, 2025

citizenM Chicago Downtown
See all 4,770 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 ￥54,896. 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.

Things to do

River tour boat in Chicago

Architecture River Tour

￥7,445
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

￥6,717
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,749
per adult
84% 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.