A curved pathway with a metal fence, flowering trees, and a street lamp.

Northwest Side Vacations from $499

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The Latest Northwest Side Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A street view with outdoor seating, a building with a sign, and tall skyscrapers in the background.
    Dec 16 - Dec 21

    The Talbott, Autograph Collection + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (199 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $739
    $499
    per traveler
    found 1 day ago
    The Talbott, Autograph Collection
  • An outdoor seating area with a fire pit, wooden benches, and tables, surrounded by large windows and string lights.
    Jan 23 - Jan 27

    The Emily Hotel + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (1,359 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $1,183
    $719
    per traveler
    found 1 day ago
    The Emily Hotel
  • The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.
    Dec 16 - Dec 21

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.4/10 - Exceptional (5,689 reviews)
    "朝食が頂ける事が素晴らしく思うと共にそのアイテムも多数あり満足でしたが、連泊しておりますと少しずつアレンジを加えて頂けますと飽きがこないと思います。"
    Reviewed November 12, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $913
    $588
    per traveler
    found 1 day ago
    Hotel Riu Plaza Chicago
  • A modern living room with a grey sofa, a round coffee table with a plant, and a TV mounted on the wall.
    Jan 23 - Jan 27

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (609 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $948
    $622
    per traveler
    found 1 day ago
    Level Chicago Fulton Market
  • A room with two chairs and a small table, a large window with a city view at night.
    Jan 22 - Jan 25

    Eurostars Magnificent Mile + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.0/10 - Wonderful (3,994 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $825
    $566
    per traveler
    found 1 day ago
    Eurostars Magnificent Mile

Discover the most popular places to visit in Northwest Side

Portage Park

After visiting Portage Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.
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Northwest Side Hotel Deals

A modern lounge area with leather sofas, a coffee table, and a patterned rug.

Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG
3.0 star property
7.3 mi from Northwest Side
9.0 out of 10, Wonderful, (3,230 reviews)
$124 nightly
The price is $141
Dec 13 - Dec 14
Total with taxes and fees
Holiday Inn Chicago O'Hare – Rosemont by IHG
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.
See all properties in Northwest Side
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.