Bridgeport Holidays from NZ$2,045

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Top Holiday Package Deals in Bridgeport

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was NZ$2,596, price is now NZ$2,045 per person
NZ$2,045
per person
4 Nov - 9 Nov
found 1 day ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.2/10 Wonderful! (2,120 reviews)
The hotel staff was great from the door men to front desk staff everyone was great.

Reviewed on 23 Sept 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was NZ$4,661, price is now NZ$3,143 per person
NZ$3,143
per person
4 Nov - 9 Nov
found 1 day ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Worth every penny! Not much more than the "average" hotel when comparing all of the amenities. Will definitely stay here again!

Reviewed on 23 Sept 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was NZ$2,946, price is now NZ$2,122 per person
NZ$2,122
per person
4 Nov - 9 Nov
found 1 day ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The room was perfect and the front staff were exceptional. Our stay was amazing!

Reviewed on 21 Sept 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was NZ$3,179, price is now NZ$2,500 per person
NZ$2,500
per person
4 Nov - 9 Nov
found 1 day ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.4/10 Exceptional! (3,344 reviews)
Close to the riverwalk

Reviewed on 23 Sept 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
Price was NZ$2,963, price is now NZ$2,347 per person
NZ$2,347
per person
4 Nov - 9 Nov
found 1 day ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.4/10 Exceptional! (2,142 reviews)
Great view and a great staff!

Reviewed on 22 Sept 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
Fully refundableReserve now, pay when you stay
7.8/10 Good! (9,228 reviews)
"Hotel is older, but very well maintained."

Reviewed on 19 Sept 2025

Get rates
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 NZ$322 per night from 20 Oct to 21 Oct
NZ$322
20 Oct - 21 Oct
includes taxes & fees
8.8/10 Excellent! (2,901 reviews)
"Great location, close to different restaurants and coffee shops. Sadly the pool was closed when I was there but it looked like the property was very well maintained. Staff was so nice upon check in. Our room was nice and comfortable! Enjoyed my stay and will be back!!"

Reviewed on 19 Sept 2025

Hilton Chicago/Magnificent Mile Suites
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
The price is NZ$361 per night from 2 Oct to 3 Oct
NZ$361
2 Oct - 3 Oct
includes taxes & fees
8.4/10 Very Good! (3,934 reviews)
"It was walking distance to Michigan Ave"

Reviewed on 21 Sept 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,579 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 NZ$2,045. 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

Bridgeport Art Center

You can spend time browsing the exhibits at Bridgeport Art Center during your travels in Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

Bridgeport Art Center

Zhou B Art Center

You can spend time browsing the exhibits at Zhou B Art Center during your trip to Chicago. Experience the acclaimed art galleries and fascinating museums in this vibrant area.

Zhou B Art Center

Activities

eSIM: Airalo United States Package

eSIM: Airalo United States Package

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

Chicago: 2-Hour Kayak Rental from Bridgeport

NZ$82
per adult
Chicago: 2-Hour Kayak Rental from Bridgeport
River tour boat in Chicago

Architecture River Tour

NZ$83
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.