Bridgeport Vacations from $679

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Your Bridgeport Vacation

Take the stress out of travel planning with a Bridgeport vacation package. With all the details locked in before you head off, all you have to do is enjoy this riverside neighborhood's cafes, dining and history. Your trip to Bridgeport wouldn't be complete without seeing major attractions nearby such as Guaranteed Rate Field, Illinois Institute of Technology and Bridgeport Art Center. Don't just think about it — take action! Book your ultimate Bridgeport vacation with Expedia and experience travel your way.

The Latest Bridgeport Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,149, price is now $679 per person
$679
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
everyone at the front desk was helpful and quite nice. room and amenities very clean. gym was well done for such a small space. would be great if there was a bathroom there. coffee and fresh fuit in the morning was awesome.

Reviewed on Jun 19, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,570, price is now $867 per person
$867
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,391 reviews)
Very clean and the breakfast was delicious!

Reviewed on Jun 20, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,611, price is now $927 per person
$927
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.

Reviewed on Jun 11, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,513, price is now $921 per person
$921
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (493 reviews)
This location is primarily a place where people live as in an apartment complex. The hotel part of it seems to be more for people doing longer stays. That means you’re not get the normal amenities or service you would get with a more traditional hotel. It is not a bad location, but I would try not to stay here again.

Reviewed on Jun 20, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,042, price is now $1,254 per person
$1,254
per person
Jul 26 - Jul 31
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,735 reviews)
Excellent hotel to stay in. Surrounded by so many things Chicago has to offer. Right across from the river. We were greeted nicely, was able to upgrade to a nicer room at a fair price. Check in was smooth. Room was very nice, well maintained hotel lobby, rooms hallways etc. had breakfast in the Land and Sea restaurant downstairs due to a rainy morning. Would definitely recommend staying at the London House for a stay in Chicago.

Reviewed on Jun 15, 2026

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

Bridgeport Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$136 nightly
The price is $162 total per night from Jun 29 to Jun 30
$162 total
Jun 29 - Jun 30
Total with taxes and fees
8/10 Very Good! (10,142 reviews)
"Amazing ceiling height and moulding...room was spacious and the view and location were epic. Felt run down and no visible activity at the restaurants made it feel a bit sad."

Reviewed on Jun 20, 2026

Congress Plaza Hotel
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
$139 nightly
The price is $166 total per night from Jul 1 to Jul 2
$166 total
Jul 1 - Jul 2
Total with taxes and fees
9/10 Wonderful! (4,451 reviews)
"Clean room exelent"

Reviewed on Jun 19, 2026

Hilton Chicago/Magnificent Mile Suites
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
$131 nightly
The price is $155 total per night from Jun 29 to Jun 30
$155 total
Jun 29 - Jun 30
Total with taxes and fees
7.8/10 Good! (1,601 reviews)
"Our stay was amazing! Staff was very helpful!"

Reviewed on Jun 19, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,681 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 Vacations
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Discover the most popular places to visit in Bridgeport

Zhou B Art Center

Enjoy a stop at Zhou B Art Center, an entertaining place to visit in Chicago. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.

Zhou B Art Center

Bridgeport Art Center

Enjoy a stop at Bridgeport Art Center, an entertaining place to visit in Chicago. Experience the acclaimed art scene and fascinating museums in this vibrant area.

Bridgeport Art Center

Palmisano Park

Palmisano Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the fascinating museums and acclaimed art scene in this vibrant area.

Palmisano Park

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$24
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
cruise ship sailing past navy pier in chicago

City Cruises Chicago: Lake Michigan Premier Dinner Cruise

$154
per adult
80% of travellers recommend
City Cruises Chicago: Lake Michigan Premier Dinner Cruise
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.