Bridgeport Holidays from AU$807

Book a Hotel + Flight or Car together to unlock savings

Your Bridgeport Holiday

Take the stress out of travel planning with a Bridgeport holiday package. With all the details locked in before you head off, all you have to do is enjoy this riverside neighbourhood's cafes, dining and history. Your trip to Bridgeport wouldn't be complete without seeing major attractions nearby such as Guaranteed Rate Field, Illinois Institute of Technology and Bridgeport Art Centre. Don't just think about it — take action! Book your ultimate Bridgeport holiday with Expedia and experience travel your way.

Top Holiday Package Deals in Bridgeport

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
30 Sept - 3 Oct
found 1 day ago
Return flight included
Dallas (DFW) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
Hard to sleep at night due to noise.

Reviewed on 20 Jul. 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
30 Sept - 3 Oct
found 1 day ago
Return flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
THE CARPET IS VERY DIRTY.

Reviewed on 21 Jul. 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
30 Sept - 3 Oct
found 1 day ago
Return flight included
Dallas (DFW) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
An amazing property and staff. Will be coming back!

Reviewed on 20 Jul. 2025

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
30 Sept - 3 Oct
found 1 day ago
Return flight included
Dallas (DFW) to Chicago (ORD)
9/10 Wonderful! (639 reviews)
The property in itself was not terrible, but I expected better.

Reviewed on 19 Jul. 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
30 Sept - 3 Oct
found 1 day ago
Return flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
This property was a great location to have access to navy pier and downtown Chicago without needing your car. The room was quite underwhelming for this pricepoint. I expect a glass drinking glass and a ceramic cup. I expect to have a bathroom with all items lotion to not smell old and have barely any in the bottle. I expect if you tell me I'm getting a complimentary $10 bottle of spring water that I'm not getting a 16 oz Dasani. I expect the drawer to close and stay closed. I expect the cooling system to function properly without being loud. I expect my parking to be included or at minimum discounted from non- guest parking. The value with this stay is mainly in the location, the view and the lovely staff, which you can find (not on the pier but near by) for a much lower price.

Reviewed on 21 Jul. 2025

Our guide on where to stay in Bridgeport

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

Our pick of the best Bridgeport Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is AU$320 per night from 4 Aug to 5 Aug
AU$320
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (8,913 reviews)
A Gem on Michigan Ave
"I was surprised at how nice my room was in this older building. The view of Buckingham fountain and the lake was the best. I was able to watch navy pier fireworks. Just an absolute pleasure and I will return!!!"

Reviewed on 21 Jul. 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is AU$498 per night from 24 July to 25 July
AU$498
24 July - 25 July
includes taxes & fees
9/10 Wonderful! (2,081 reviews)
"Love the pool and the history of the hotel..will make it a yearly adventure"

Reviewed on 20 Jul. 2025

InterContinental Chicago Magnificent Mile by IHG
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 AU$259 per night from 17 Aug to 18 Aug
AU$259
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (2,494 reviews)
"Loved it!"

Reviewed on 20 Jul. 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,640 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.
All Inclusive Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Bridgeport holiday package cost?
From as little as AU$807. 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.

Discover the most popular places to visit in Bridgeport

Bubbly Creek

Commune with nature and explore the great outdoors at Bubbly Creek during your travels in Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.

Bubbly Creek

Activities

River tour boat in Chicago

Architecture River Tour

AU$75
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$69
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

AU$69
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
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.