A train crossing an elevated bridge over a city street with buildings and greenery.

Wicker Park Vacations from $415

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Wicker Park Vacation

Lock in a vacation package to Wicker Park and get set to experience its nightlife, bars and pubs and cafes. However you plan to spend your stay in this food-lovers neighborhood, there are plenty of opportunities for fun and relaxation. Your trip to Wicker Park wouldn't be complete without exploring leading attractions nearby such as University of Illinois Chicago, United Center and Humboldt Park. No matter your travel goals or the size of your budget, booking your dream Wicker Park vacation has never been easier with Expedia.

The Latest Wicker Park Vacation Packages

Price found within the past 48 hours. Click for updated prices.
  • A rooftop lounge with outdoor seating and a city skyline view.
    Dec 16 - Dec 19

    Pendry Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,162 reviews)
    "Beautiful rooms and service."
    Reviewed November 5, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    Save 100% on your flight
    $617
    $415
    per traveler
    found 1 day ago
    Pendry Chicago
  • A cityscape with modern high-rise buildings, a river, and a bridge.
    Dec 21 - Dec 24

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,875 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $1,880
    $446
    per traveler
    found 1 day ago
    Sheraton Grand Chicago Riverwalk
  • The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.
    Dec 17 - Dec 21

    Hotel Riu Plaza Chicago + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (5,647 reviews)
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $826
    $541
    per traveler
    found 2 days 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.
    Dec 28 - Jan 1

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    9.2/10 - Wonderful (602 reviews)
    "If you are looking to stay in a condo type setting, this may be your spot. I checked in which you need to go through a process that takes 15 minutes, (do it before) and they automatically add a $25 per night fee for their gym and roof top. This was NOT published on Hotels.com or any other site. A total rip off as this is not a spa. There was no housekeeping. Checking in took 15 minutes in which there was little to no Wifi, so I had to go do this outside (crazy?). Do the check-in before..."
    Reviewed November 4, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - ORD • Nonstop ORD - ATL • Nonstop
    $931
    $631
    per traveler
    found 1 day ago
    Level Chicago Fulton Market
  • A modern living room with a sofa, chairs, a coffee table, and a TV. A large window offers a view of a cityscape and a tower.
    Dec 10 - Dec 13

    Park Hyatt Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,001 reviews)
    "Given the price point and other reviews, we came here expecting a luxury stay similar to the Waldorf Astoria, Four Seasons, and Peninsula, which are some of our favorite properties to stay at. However, everything from the service and cleanliness to the ambiance of the entrance and lobby and the amenities (other than the gym, which was excellent) is best described as an upgraded version of an average Hilton, Hyatt, or Marriott. For example, there was a hair in the bed. When we reported it, the..."
    Reviewed November 4, 2026
    Roundtrip • Atlanta (ATL) - Chicago (ORD)
    ATL - MDW • Nonstop ORD - ATL • Nonstop
    $1,826
    $1,237
    per traveler
    found 7 hours ago
    Park Hyatt Chicago

Where to stay in Wicker Park

Find the best Wicker Park areas and neighborhoods for the activities you enjoy most. Learn more about Wicker Park
Learn more about Wicker Park
A cityscape with tall skyscrapers and a historic tower.

Downtown Chicago

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

A busy urban street at dusk with tall buildings, a historic tower, and pedestrians.
Photo by © City of Chicago
Open Photo by © City of Chicago

Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

A river with yellow boats, a bridge, and tall buildings.

The Loop

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

A large, historic building with a central tower and multiple windows, located near a body of water.

River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

A river with a city skyline in the background, surrounded by green trees and grass.

Lincoln Park

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

Discover the most popular places to visit in Wicker Park

Subterranean

You can enjoy a show at Subterranean during your stay in Chicago. Experience the live music and theater scene in this vibrant area.
See properties

What to do near Wicker Park

360 CHICAGO Observation Deck (Hancock Center)

360 CHICAGO Observation Deck

$24
per adult
86% of travelers recommend
360 CHICAGO Observation Deck
See all activities near Wicker Park

Wicker Park Hotel Deals

A breakfast setting with a plate of toast, a bowl of fruit, a cup of coffee, and a newspaper on a table by a window with a city view.

The Robey, Chicago, a Member of Design Hotels

The Robey, Chicago, a Member of Design Hotels
3.5 star property
Wicker Park
9.2 out of 10, Wonderful, (1,000 reviews)
"Clean room, but the air ducts are in the room and you can hear the dampers opening and closing at night. Parking is valet parking and is $49. Which isn’t bad for Chicago. In a great location if you are visiting someone in Wicker Park. The blue line stop is just across the street."
$183 nightly
The price is $214
Nov 23 - Nov 24
Total with taxes and fees
The Robey, Chicago, a Member of Design Hotels
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 Wicker Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.