Apartment vacation rentals in Bridgeport, Chicago
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Top-rated apartment rentals in Bridgeport, Chicago
Guests agree: these apartments are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Bridgeport, Chicago apartment rentals
Weekly apartment rentals
Apartment in Chicago
4.98 out of 5 average rating, 297 reviewsRedesigned Lower Level Studio in Historic Building
Oct 16 – 23
Apartment in Chicago
4.92 out of 5 average rating, 152 reviewsUrban Pilsen Apt. near Downtown
Feb 10 – 17
Apartment in Little Italy
4.98 out of 5 average rating, 198 reviewsSpacious 2BR on Quiet St - Free Park/Late Checkout
Dec 29 – Jan 5
Apartment in Chicago
4.96 out of 5 average rating, 262 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Mar 30 – Apr 6
Apartment in Chicago
4.91 out of 5 average rating, 111 reviewsNEW Modern 2BRD apartment| 5min to McCormick Place
Sep 23 – 30
Apartment in Chicago
4.85 out of 5 average rating, 273 reviewsHUGE|3br/2ba/Near DT/Free Parking/WI-FI/Pilsen
Nov 18 – 25
Apartment in Chicago
4.82 out of 5 average rating, 429 reviewsEclectic Artist Designed Sanctuary Heart of Pilsen
Oct 17 – 24
Apartment in Oak Park
4.89 out of 5 average rating, 334 reviewsCharming Chicago-Style, Vintage, Tv NFL PASS
Sep 27 – Oct 4
Private apartment rentals
Apartment in Oak Park
4.85 out of 5 average rating, 529 reviewsLong stays welcome@warm&cute vintage 2BR
Sep 26 – Oct 3
Apartment in Chicago
4.87 out of 5 average rating, 216 reviewsGarden Apartment in the Historic Heart of the City
Aug 11 – 18
Apartment in Oak Park
4.91 out of 5 average rating, 104 reviewsLovely, spacious 2bd, 1bath home w/free parking
Sep 29 – Oct 6
Apartment in Chicago
4.81 out of 5 average rating, 270 reviewsThe Banksy-Greystone Rooftop Firepit United Center
Apartment in Forest Park
4.92 out of 5 average rating, 112 reviewsVillage Cottage - Forest Park Studio Pets 72142F
May 7 – 14
Apartment in Chicago
4.95 out of 5 average rating, 124 reviewsCozy 2 bdrm near McCormick Place & Wintrust Arena
Jul 3 – 10
Apartment in Chicago
4.97 out of 5 average rating, 236 reviewsStylish First Flr. Studio. Best Location Division+Hermitage.
Nov 18 – 25
Apartment in Forest Park
4.98 out of 5 average rating, 285 reviewsWalk to Oak Park from Our Sunny Turn of the Century Apt
Sep 21 – 28
Apartment rentals with a hot tub
Apartment in Chicago
4.87 out of 5 average rating, 156 reviewsStunning Panoramic Chicago Views & Free Parking
Nov 1 – 8
Apartment in Berwyn
4.91 out of 5 average rating, 203 reviews“Dream slice of urban homesteading.”
Nov 29 – Dec 6
Apartment in Chicago
4.88 out of 5 average rating, 393 reviewsCheckerboard Studio with Private Outdoor Hot Tub and Yard
Oct 14 – 21
Apartment in Chicago
4.87 out of 5 average rating, 106 reviewsCloud9 |XL Penthouse+Movie Theater+Gym |The Harper
Feb 18 – 25
Apartment in Chicago
4.9 out of 5 average rating, 30 reviewsLuxe Suite + Spa House Retreat! Pets Welcome
Mar 8 – 15
Apartment in Chicago
4.87 out of 5 average rating, 45 reviewsSpectacular Rooftop Getaway in Heart of City
Jun 23 – 30
Apartment in Chicago
4.78 out of 5 average rating, 9 reviewsThe Areal Oasis
Sep 18 – 25
Apartment in Chicago
5.0 out of 5 average rating, 10 reviewsLake, City, & River View Condo
Jul 10 – 17
Quick stats about apartment rentals in Bridgeport, Chicago
Total rentals
90 properties
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
50 properties are a good fit for families
Total number of reviews
2.7K reviews
Nightly prices starting at
$20 before taxes and fees
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