Bridgeport Holidays from £669

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Your Bridgeport Holiday

Immerse yourself in the beauty of this riverside neighbourhood with a Bridgeport holiday package. From its cafes and dining to its history, there's lots here for every type of holiday maker. Want to get out and see the sights during your trip to Bridgeport? Don't miss nearby attractions like Willis Tower, University of Illinois Chicago and Skydeck Ledge. No matter what your dream Bridgeport holiday may look like, you can make it a reality with Expedia.

Price found within the past 48 hours. Click for updated prices.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,050, price is now £669 per person
£669
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
Rooms are basic and bathrooms and sink area small. But all comfortable

Reviewed on 17 Aug 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,724, price is now £1,037 per person
£1,037
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,033 reviews)
Loved the atmosphere and friendly atmosphere

Reviewed on 18 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,385, price is now £839 per person
£839
per person
6 Nov - 10 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,576, price is now £982 per person
£982
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,359 reviews)
Shawn at the front desk was awesome. It was our first time in Chicago and we loved staying at LondonHouse!

Reviewed on 19 Aug 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,266, price is now £807 per person
£807
per person
20 Sept - 27 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Friendly staff, clean and comfortable, convenient location

Reviewed on 20 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 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

Top hotels in Bridgeport

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
The price is £117 per night from 1 Sept to 2 Sept
£117
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (9,014 reviews)
"Great hotel"

Reviewed on 20 Aug 2025

Congress Plaza Hotel
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £131 per night from 1 Sept to 2 Sept
£131
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,205 reviews)
"The pool could have been a bit better"

Reviewed on 19 Aug 2025

The Wade
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
The price is £140 per night from 3 Sept to 4 Sept
£140
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,726 reviews)
"Valet parking was very expensive for leaving your car without using it for 2 days."

Reviewed on 20 Aug 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,691 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
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Bridgeport travel package cost?
From as low as £669, you can custom build your Bridgeport package the way you want. Simply combine hotels, flights and car rentals and we'll reward you with discounts.
If I'm not able to travel, can I cancel my Bridgeport travel package?
We totally understand — life doesn't always go according to plan. If you've booked a Bridgeport travel package and have to change or cancel it, we're here to help. We recommend checking out our Customer Service Portal first for information. But generally, if you've booked your package in the last 24 hours, you may be able to amend or cancel your itinerary at no cost. If it's been longer than 24 hours, your airline, hotel or car rental company may impose a charge.
How do I get a cheap travel package to Bridgeport?
Combining your flight and hotel with Expedia won't just save valuable time — it'll save you dollars too. A Bridgeport travel package makes it simple to put together your dream adventure. With more than 550 airlines worldwide to pick from, finding flights that fit your busy schedule won't be hard. On top of that, we've got over 1,000,000 hotel options globally to take your pick of. Now that's choice! No matter who you are, Expedia brings the world within your reach.
Does Expedia offer Book Now, Pay Later Bridgeport holidays?
Your bank balance shouldn't get in the way of taking a holiday, so Expedia has worked out a solution to help. Now that we've formed a partnership with online lender Klarna, it's easier than ever to book a terrific getaway without draining your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your break. Check out these flexible payment options:

  • Pay monthly holidays: Make your holiday dreams come true sooner with Klarna's manageable monthly instalment plans. If paying just a small amount each month sounds right for you, choose this option during the checkout process.
  • Pay in instalments holidays: If you want to pay off your escape in multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than all of it upfront) makes it easier to hit that "book now" button, go for a low deposit holiday payment plan with Klarna.

Where should I stay in Bridgeport?
A trip to Bridgeport isn't complete until you've seen Millennium Park and Wrigley Field. Stay at a hotel as close as possible and easily access these impressive sights.
What are the top hotels in Bridgeport?
Hyatt Regency Chicago and The Godfrey Hotel Chicago are two of the most well-known hotels in Bridgeport. Why not look up the facilities and rates at each and then make up your mind?
How far in advance should I book my Bridgeport holiday?
Browse Expedia to compare international airfares as early as possible. You can generally purchase a ticket up to a year prior to departure. If you can't see your preferred carrier, or you're booking late, fear not. Cheap fares to Bridgeport sometimes appear within weeks of the date of departure.
What does an Expedia Bridgeport travel package include?
Choose from a combination of rental cars, flights and hotels. Once you've made your booking, you can also add on activities and experiences. Want to pick your airfare class? That's easily done too. The choice is all yours when it comes to planning your ideal Bridgeport getaway.
What should I know before booking a Bridgeport travel package?
A travel package can be cheaper than individually booking everything you need for your adventure. For example, bundle your hotels, flights and rental cars and save a packet. No matter your holiday goals, you're bound to find a package that best suits your budget.
Can I choose my airline with a Bridgeport Expedia travel package?
Yes, the choice is all yours. We have access to over 550 airlines around the world, so you can tailor your Bridgeport getaway according to your travel preferences.

Things to do

eSIM: Airalo United States Package

eSIM: Airalo United States Package

£1
per traveller
eSIM: Airalo United States Package
Chicago: 2-Hour Kayak Rental from Bridgeport

Chicago: 2-Hour Kayak Rental from Bridgeport

£36
per adult
Chicago: 2-Hour Kayak Rental from Bridgeport
River tour boat in Chicago

Architecture River Tour

£31
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. Flight-inclusive packages are ATOL protected.