Bridgeport Vacations from $602
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
The Latest Bridgeport Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Hotel Felix River North/Magnificent Mile
Aug 20 - Aug 24Hotel Felix River North/Magnificent Mile + Flight
Downtown Chicago4 nights4.0 star property8.2/10 - Very Good (2,848 reviews)"Nice staff, easy check-in, and about an 8 minute walk to red line which can get you all over town. No complaints about our stay."Reviewed July 18, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop ORD - ATL • Nonstop - Level Chicago – Old Town
Sep 30 - Oct 5Level Chicago – Old Town + Flight
Downtown Chicago5 nights4.0 star property9.0/10 - Wonderful (502 reviews)"Overall, I had a pleasant stay. The room was clean, and the staff were helpful. The property was comfortable and family-friendly. The only improvement would be better Wi-Fi and more breakfast options. I would still recommend this place."Reviewed July 14, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Hotel Saint Clair- Magnificent Mile
Aug 26 - Aug 30Hotel Saint Clair- Magnificent Mile + Flight
Downtown Chicago4 nights4.0 star property8.4/10 - Very Good (2,041 reviews)"Clean room but the bathroom is the smallest one I've experienced in a hotel."Reviewed July 18, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - ORD • Nonstop ORD - ATL • Nonstop - Hotel Riu Plaza Chicago
Aug 20 - Aug 24Hotel Riu Plaza Chicago + Flight
Downtown Chicago4 nights4.0 star property9.4/10 - Exceptional (4,749 reviews)"The room and hotel exceeded my expectations. The hotel was located in the best spot. I would definitely stay here again."Reviewed July 18, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop ORD - ATL • Nonstop - Level Chicago Fulton Market
Aug 20 - Aug 24Level Chicago Fulton Market + Flight
Downtown Chicago4 nights4.0 star property9.2/10 - Wonderful (528 reviews)"Staff was amazing—so helpful, attentive, and hands-on throughout our stay. The room was absolutely gorgeous, and the view was beautiful. Everything exceeded our expectations, and we had a wonderful experience!"Reviewed July 17, 2026Roundtrip • Atlanta (ATL) - Chicago (ORD)ATL - MDW • Nonstop ORD - ATL • Nonstop
Discover the most popular places to visit in Bridgeport
What to do near Bridgeport
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travelers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travelers recommend
Bridgeport Hotel Deals
Holiday Inn & Suites Chicago - Downtown by IHG
Holiday Inn & Suites Chicago - Downtown by IHG3.0 star property
West Loop, 2.7 mi from Bridgeport
8.6 out of 10, Excellent, (1,082 reviews)
8.6/10
Excellent
(1,082 reviews)
$157 nightly
The price is $187
$187 total
Aug 9 - Aug 10
Total with taxes and fees
Hilton Garden Inn Chicago Downtown South Loop
Hilton Garden Inn Chicago Downtown South Loop3.0 star property
The Loop, 2.6 mi from Bridgeport
8.8 out of 10, Excellent, (2,084 reviews)
8.8/10
Excellent
(2,084 reviews)
"Must staff were pleasant."
$163 nightly
The price is $194
$194 total
Aug 10 - Aug 11
Total with taxes and fees
Best Western Grant Park Hotel
Best Western Grant Park Hotel2.5 star property
The Loop, 2.6 mi from Bridgeport
8.2 out of 10, Very Good, (2,745 reviews)
8.2/10
Very Good
(2,745 reviews)
$161 nightly
The price is $192
$192 total
Aug 9 - Aug 10
Total with taxes and fees
Homewood Suites by Hilton Chicago Downtown South Loop
Homewood Suites by Hilton Chicago Downtown South Loop3.0 star property
The Loop, 2.6 mi from Bridgeport
8.8 out of 10, Excellent, (2,393 reviews)
8.8/10
Excellent
(2,393 reviews)
"We liked that the staff was helpful. The hotel is located in a very convenient location being walking distance to many shops, restaurants and a jazz club. Nice area!
What we didn’t like: Breakfast could be better."
$167 nightly
The price is $199
$199 total
Aug 9 - Aug 10
Total with taxes and fees
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG3.5 star property
3.1 mi from Bridgeport
9.0 out of 10, Wonderful, (2,393 reviews)
9.0/10
Wonderful
(2,393 reviews)
$188 nightly
The price is $224
$224 total
Aug 13 - Aug 14
Total with taxes and fees
Travelodge by Wyndham Downtown Chicago
Travelodge by Wyndham Downtown Chicago2.0 star property
The Loop, 2.9 mi from Bridgeport
7.6 out of 10, Good, (2,690 reviews)
7.6/10
Good
(2,690 reviews)
"Misrepresentation of rooms I thought was at Bates Motel A/C in the window I’m from Louisiana and I have never seen a hotel room look that way I would never stay there ever in my life"
$167 nightly
The price is $199
$199 total
Aug 19 - Aug 20
Total with taxes and fees
9.0 out of 10, Wonderful, (1,003 reviews)
9.0/10
Wonderful
(1,003 reviews)
$190 nightly
The price is $226
$226 total
Aug 9 - Aug 10
Total with taxes and fees
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel4.0 star property
The Loop, 2.9 mi from Bridgeport
9.6 out of 10, Exceptional, (1,286 reviews)
9.6/10
Exceptional
(1,286 reviews)
$183 nightly
The price is $218
$218 total
Aug 9 - Aug 10
Total with taxes and 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.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.