Bridgeport Holidays from £1,183

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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 Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,538, price is now £1,183 per person
£1,183
per person
29 Sept - 6 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
7.8/10 Good! (1,665 reviews)
Ourdoor terrace was closed for renovation

Reviewed on 13 Jul 2026

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,790, price is now £1,299 per person
£1,299
per person
29 Sept - 6 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
8.4/10 Very good! (2,006 reviews)
The staff was great. The bed was nice and comfy. The shower floor wasn't fully white and a towel looked stained. Overall, it was a decent stay.

Reviewed on 13 Jul 2026

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago

4.5 out of 5
Downtown Chicago
Price was £2,979, price is now £2,282 per person
£2,282
per person
29 Sept - 6 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
Hotel was great! However, you tricked me and send me back to a wrong airport. That’s costing me money and time. I won’t use your app anymore. I can’t trust you.

Reviewed on 6 Jul 2026

Hotel 55 Chicago Downtown

Hotel 55 Chicago Downtown

4 out of 5
Downtown Chicago
Price was £1,796, price is now £1,391 per person
£1,391
per person
29 Sept - 6 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
8.8/10 Excellent! (1,573 reviews)
I would stay here again when I am in Chicago. The only issue I had was a faint sewer smell in my room that cane and went throughout my stay. I was only in my room at night so I wasn’t sure if it smelled that way during the day. I informed the front desk. Other than that this was a perfect quiet convenient location.

Reviewed on 14 Jul 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,812, price is now £1,416 per person
£1,416
per person
27 Sept - 1 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Room was clean area was fines. Staff was mediocre at best. Last night person seem disinterested and didn’t seem to want to speak. For the price we paid it was honestly not work it too me. Felt that they nickeled and dined you too death. No housekeeping for the entire 5 night. Crazy expensive for parking we had to make other arrangements which was a hassle since i was on crutches but we made it work. Even if we had parties on garage not elevator access. Will not be staying here again. Not worth the money, poor customer service. Had to get towels and empty trash daily. Very disappointing!!

Reviewed on 13 Jul 2026

Where to stay in Bridgeport

Find the best Bridgeport areas and neighborhoods for the activities you enjoy most. Learn more about Bridgeport
A busy city street with tall buildings, a bus, and cars.

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

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is £144 per night from 4 Aug to 5 Aug
£144
4 Aug - 5 Aug
includes taxes & fees
8.8/10 Excellent! (2,840 reviews)
"This is the third time we’ve stayed, and every time we’ve enjoyed, property is well kept, nice rooms, great staff, wonderful breakfast, would definitely recommend!"

Reviewed on 14 Jul 2026

Hyatt Regency O'Hare Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is £146 per night from 27 Jul to 28 Jul
£146
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very good! (1,747 reviews)
"We decided to extend our stay and the staff were amazing. Very courteous !!!"

Reviewed on 13 Jul 2026

The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is £234 per night from 26 Jul to 27 Jul
£234
26 Jul - 27 Jul
includes taxes & fees
9.2/10 Wonderful! (1,917 reviews)
"While amenities and being up to date are important, my main focus for a hotel is it’s cleanliness and how comfortable is the bed since I’ve stayed many places that while nice, if the bed is uncomfortable can ruin your stay. Our room at Omni was clean and comfortable. There were a few things that ..."

Reviewed on 13 Jul 2026

Omni Chicago Hotel
See all 4,521 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
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Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Bridgeport travel package cost?
From as low as £1,183, 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 fascinating museums and acclaimed theatre scene in this vibrant area.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£19
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Flyover in Chicago

Flyover in Chicago

£24
per adult
96% of travellers recommend
Flyover in Chicago
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.