Bridgeport Holidays

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

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.
  • Indoor wedding
    Aug 3 - Aug 8

    Swissotel - Chicago + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.0/10 - Wonderful (3,351 reviews)
    "From the fitness center to the restaurant, all facilities are well maintained by staff and they were helpful with all requests."
    Reviewed May 26, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • Direct ORD - LHR • Direct
    £1,867
    £1,354
    per traveller
    found 1 day ago
    Swissotel - Chicago
  • Premium bedding, pillow-top beds, in-room safe, individually furnished
    Jul 4 - Jul 11

    Level Chicago - River North + Flight

    Downtown Chicago
    7 nights
    4.0 star property
    9.2/10 - Wonderful (1,011 reviews)
    "I loved everything."
    Reviewed May 25, 2026
    Return • Aberdeen (ABZ) - Chicago (ORD)
    ABZ - ORD • 1 stop ORD - ABZ • 1 stop
    Save 100% on your flight
    £3,557
    £2,423
    per traveller
    found 2 days ago
    Level Chicago - River North
  • Smart TV
    Aug 2 - Aug 7

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.2/10 - Wonderful (488 reviews)
    "Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely."
    Reviewed May 22, 2026
    Return • London (LHR) - Chicago (ORD)
    LHR - ORD • 2 stops ORD - LHR • 2 stops
    £1,950
    £1,374
    per traveller
    found 1 day ago
    Level Chicago Fulton Market
  • Full-sized fridge, microwave, oven, stovetop
    Jul 4 - Jul 11

    Level Chicago – Old Town + Flight

    Downtown Chicago
    7 nights
    4.0 star property
    9.0/10 - Wonderful (481 reviews)
    "Nice and big"
    Reviewed May 24, 2026
    Return • Aberdeen (ABZ) - Chicago (ORD)
    ABZ - ORD • 1 stop ORD - ABZ • 1 stop
    £2,220
    £1,640
    per traveller
    found 2 days ago
    Level Chicago – Old Town
  • Terrace/patio
    Jul 4 - Jul 11

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    7 nights
    5.0 star property
    9.6/10 - Exceptional (1,886 reviews)
    "Location, cleanliness, overall staff assistance and service and of course breakfast"
    Reviewed May 26, 2026
    Return • Aberdeen (ABZ) - Chicago (ORD)
    ABZ - ORD • 1 stop ORD - ABZ • 1 stop
    £2,896
    £2,185
    per traveller
    found 2 days ago
    Trump International Hotel & Tower Chicago

Where to stay in Bridgeport

Find the best Bridgeport areas and neighborhoods for the activities you enjoy most. Learn more about Bridgeport
Downtown Chicago

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 £119 per night from 27 May to 28 May
£119
27 May - 28 May
includes taxes & fees
8/10 Very Good! (10,141 reviews)
"Everything was perfect. Great customer service."

Reviewed on 25 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is £232 per night from 16 Jun to 17 Jun
£232
16 Jun - 17 Jun
includes taxes & fees
9.4/10 Exceptional! (4,253 reviews)
"The hotel is clean and in a good location. The bathrooms are spacious and the showers were excellent. The rooms, however, are long, narrow, and cheaply furnished, with awkward closets and water-restricted faucets. The hotel feels designed to cut costs, without passing any savings to guests. Tile ..."

Reviewed on 26 May 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is £162 per night from 24 Jun to 25 Jun
£162
24 Jun - 25 Jun
includes taxes & fees
7.8/10 Good! (1,477 reviews)
"El staff es un poco malhumorado Cuando tienes preguntas, la mayoria. Los tickets de comida o drinks gratis en realidad son descuentos, tienes q pagar. Excepto por el desayuno, solo use una vez cada uno, no me agrado, sali afuera. Regrese todos los demas tickets al hacer checkout. Gracias"

Reviewed on 26 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,756 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 , 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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

£16
per child
98% 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.