Bridgeport Holidays from £865
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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.
Hotel Riu Plaza Chicago
Downtown Chicago
£988
per person
15 Nov - 22 Nov
found 2 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
The staff were helpful, the room was nice and clean, and the buffet breakfast was amazing. We enjoyed our stay.
Reviewed on 28 Aug 2026
Where to stay in Bridgeport
Find the best Bridgeport areas and neighborhoods for the activities you enjoy most. Learn more about Bridgeport
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.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Top hotels in Bridgeport
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£92
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,198 reviews)
"It was clean and friendly"
Reviewed on 28 Aug 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
£125
31 Aug - 1 Sept
includes taxes & fees
8/10 Very good! (2,113 reviews)
"Staff was very nice, hotel is in a great location"
Reviewed on 28 Aug 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
£200
18 Sept - 19 Sept
includes taxes & fees
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 travel package cost?
From as low as £865, 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.
Stay near popular Bridgeport attractions
Bridgeport Art Center
Enjoy a stop at Bridgeport Art Center, an entertaining place to visit in Chicago. Experience the acclaimed theatre scene and fascinating museums in this vibrant area.
Zhou B Art Center
Enjoy a stop at Zhou B Art Center, an entertaining place to visit in Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.
Ramova Theatre
You can get tickets for a performance at Ramova Theatre on your trip to Chicago. Discover the area's entertainment choices and churches.
Theatre on the Lake
You can make plans for a show at Theatre on the Lake on your trip to Chicago. Stroll along the lakeside or experience the acclaimed art galleries in this vibrant area.
Stephen A. Douglas Tomb and Memorial
Find out about the history of Chicago when you spend time at Stephen A. Douglas Tomb and Memorial. Experience the fascinating museums and acclaimed theatre scene in this vibrant area.
Palmisano Park
Palmisano Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the acclaimed art galleries and entertainment choices in this vibrant area.
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
£35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
£18
per adult
90% of travellers recommend
* 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.