Bridgeport Holidays from £842

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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.
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
per person
11 Sept - 16 Sept
found 6 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.2/10 Very Good! (2,069 reviews)
Item was left in room. I tried for days to get contact with front desk and security will little to no luck. They say nothing reported so I consider that as theft by staff. Very disappointing.

Reviewed on 2 Jul 2025

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
4 Aug - 11 Aug
found 16 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
I had such a lovely staycation, and I recommend a stay here to everyone I know.

Reviewed on 26 Jun 2025

The Hoxton Chicago

The Hoxton Chicago

4 out of 5
Downtown Chicago
per person
4 Aug - 11 Aug
found 10 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The pool hours are a bit of a deal breaker. The pool closes at 4pm because they don’t want to offend their dining guests. So no relaxing swim after a day of site seeing in the heat unless you cut things short and rush back. This hotel needs to decide if it is a hotel or a dining and nightclub (a LOUD one..) destination. The staff was generally nice, but this will not be a repeat experience.

Reviewed on 29 Jun 2025

Hyatt Lodge Oak Brook Chicago

Hyatt Lodge Oak Brook Chicago

4 out of 5
per person
18 Sept - 23 Sept
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.8/10 Excellent! (1,008 reviews)
Parking lot under construction messing amd challenging to get to main entrance. Front desk staff pleasant and very helpful. Inner building lacked clear instruction to locate pool, sauna steam room. Rooms were excellent bed super comfy. Disappointed in breakfast i miss understood i thought set up was brunch. Overall ok nearby Oak Brook mall and fine eatry. Review other spa like lodges before locking into this location. Happy travels....

Reviewed on 3 Jul 2025

21c Museum Hotel Chicago

21c Museum Hotel Chicago

4 out of 5
Downtown Chicago
per person
11 Sept - 16 Sept
found 16 hours ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
8.6/10 Excellent! (1,719 reviews)
Located near shopping and restaurants. Easy access to Red Line trains. Rooms were smaller than expected. Not as nice as other 21c hotels. Hallways were dark and beaten up. Service was friendly. Restaurant had great happy hour.

Reviewed on 2 Jul 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

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 £136 per night from 10 Jul to 11 Jul
£136
10 Jul - 11 Jul
includes taxes & fees
8.8/10 Excellent! (2,367 reviews)
"Staff were really nice and accommodating. I was able to check in early and check out late for free. The room was decent. Outdated but it was clean. Would book again."

Reviewed on 2 Jul 2025

Hilton Chicago/Magnificent Mile Suites
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
The price is £219 per night from 6 Jul to 7 Jul
£219
6 Jul - 7 Jul
includes taxes & fees
9/10 Wonderful! (1,965 reviews)
"We enjoyed our stay at the Intercontinental! Great rooms. Clean. Great service. Will stay again."

Reviewed on 3 Jul 2025

InterContinental Chicago Magnificent Mile by IHG
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £102 per night from 7 Jul to 8 Jul
£102
7 Jul - 8 Jul
includes taxes & fees
7.8/10 Good! (8,864 reviews)
"Decent stay for a few nights"

Reviewed on 3 Jul 2025

Congress Plaza Hotel
See all 4,540 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 £842, 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
River tour boat in Chicago

Architecture River Tour

£36
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£33
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture 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.