Bridgeport Vacation Packages 2025/2026 from $445

Bridgeport flight + hotel vacation packages

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

La Banque Hotel

Save 100% on your flight

per person

Aug 29 - Sep 1

found 21 hours ago

Roundtrip flight included

Minneapolis (MSP) to Chicago (ORD)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and concierge services.

Park Hyatt Chicago

Downtown Chicago

Save 100% on your flight

per person

Oct 5 - Oct 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.

The Langham, Chicago

Downtown Chicago

Save 100% on your flight

per person

Oct 4 - Oct 7

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and laundry facilities.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

per person

Oct 5 - Oct 8

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

A restaurant is on site and multilingual staff is available around-the-clock at the 24-hour front desk. Unwind with a drink at one of the 2 bars/lounges and enjoy free perks like buffet breakfast and WiFi in public areas. There's a 24-hour gym on site, and a coffee shop and a snack bar/deli are also provided.

Trump International Hotel & Tower Chicago

Downtown Chicago

Save 100% on your flight

per person

Sep 26 - Sep 28

found 1 day ago

Roundtrip flight included

Boston (BOS) to Chicago (ORD)

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.

Top Bridgeport hotels deals

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$169 nightly

$199 total

Aug 10 - Aug 11

Total includes taxes and fees

This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.

Free WiFi

Restaurant

InterContinental Chicago Magnificent Mile by IHG

505 N Michigan Ave, Chicago, IL

Free Cancellation

$276 nightly

$318 total

Aug 22 - Aug 23

Total includes taxes and fees

This luxury hotel includes 2 restaurants, an indoor pool, and a gym. Enjoy the steam room and perks like free WiFi. A bar/lounge, a 24-hour front desk, and a coffee shop are also provided.

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl, Chicago, IL

Free Cancellation

Reserve now, pay when you stay

$144 nightly

$169 total

Aug 17 - Aug 18

Total includes taxes and fees

A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.

Pet friendly

Free WiFi

Crowne Plaza Chicago West Loop by IHG

25 South Halsted Street, Chicago, IL

Free Cancellation

$150 nightly

$176 total

Aug 24 - Aug 25

Total includes taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a snack bar/deli are also offered.

Embassy Suites by Hilton Chicago Downtown River North

600 N State St, Chicago, IL

$165 nightly

$193 total

Aug 24 - Aug 25

Total includes taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and a grocery/convenience store are also offered.

citizenM Chicago Downtown

80 East Wacker Place, Chicago, IL

$156 nightly

$184 total

Aug 26 - Aug 27

Total includes taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, a communal living room, and express check-in are also on offer.

Free WiFi

Restaurant

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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.

Popular places to visit

Bridgeport Art Center

You can spend time studying the exhibits at Bridgeport Art Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

Zhou B Art Center

You can spend time studying the exhibits at Zhou B Art Center during your trip to Chicago. Experience the acclaimed art scene and entertainment choices in this vibrant area.

Theatre on the Lake

You can make plans for a show at Theatre on the Lake during your stay in Chicago. Stroll along the lakeside or experience the acclaimed theater scene in this vibrant area.

Frequently asked questions

How much are vacation packages to Bridgeport?

Exciting adventures await in Bridgeport, with Travelocity vacation packages starting at just $445. In addition to flights and hotels, these amazing deals make it easy to see more of our beautiful planet.

Where can I get the best vacation package deals for Bridgeport?

Travelocity has countless ways to score an amazing Bridgeport package deal. Choose from 400 airlines and 1,000,000 hotels worldwide and put together a vacation package that's right for you. With so many options at hand, now's the time to book your next big getaway.

Why should I purchase my Bridgeport vacation package with Travelocity?

You'll not only save lots, but you can also access our 24/7 support, top-notch service and a Price Match Guarantee. Wander across the world, discover hidden treasures and forge long-lasting memories — we'll take care of the little details.

Can I save on my Bridgeport car rental if I combine it with a hotel or flight?

Booking a Bridgeport vacation package with Travelocity is one of the best ways to save cold, hard cash. Combine a hotel, car and flight, or any combination of them, and land awesome discounts. You might also want to throw in experiences. Once you've collected the keys to the rental car, head out of the neighborhood and discover what the surrounding area has to offer. About 40 mi from Bridgeport, Six Flags Great America is well worth a road trip.

What is there to do in Bridgeport?

Bridgeport Art Center and Zhou B Art Center are much loved by so many travelers. Check these places off your Bridgeport itinerary and discover what the hype is about.