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A city skyline with illuminated buildings, a river, and a bridge.

Bridgeport Vacations from $440

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The Latest Bridgeport Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Sep 25 - Sep 28

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.2/10 - Very Good (2,844 reviews)
    "Great location, clean room, super quiet hotel, great staff. Definitely recommend!"
    Reviewed July 17, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $688
    $440
    per traveler
    found 1 day ago
    Hotel Felix River North/Magnificent Mile
  • Front of property
    Sep 3 - Sep 8

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.4/10 - Exceptional (4,742 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - MDW • Nonstop MDW - ATL • Nonstop
    Save 100% on your flight
    $1,602
    $967
    per traveler
    found 1 day ago
    Hotel Riu Plaza Chicago
  • Full-size fridge, microwave, oven, stovetop
    Sep 25 - Sep 29

    Level Chicago – Old Town + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.0/10 - 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, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $1,238
    $751
    per traveler
    found 1 day ago
    Level Chicago – Old Town
  • Premium bedding, pillowtop beds, in-room safe, desk
    Sep 10 - Sep 13

    Level Chicago - River North + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.2/10 - Wonderful (1,036 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $849
    $519
    per traveler
    found 1 day ago
    Level Chicago - River North
  • Indoor wedding
    Sep 25 - Sep 28

    Swissotel - Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.0/10 - Wonderful (3,496 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $885
    $561
    per traveler
    found 1 day ago
    Swissotel - Chicago

Discover the most popular places to visit in Bridgeport

Bridgeport Art Center

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

What to do near Bridgeport

360 CHICAGO Observation Deck (Hancock Center)

360 CHICAGO Observation Deck

$22
per adult
86% of travelers recommend
360 CHICAGO Observation Deck
See all activities near Bridgeport