Wicker Park Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €900 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
Price found within the past 48 hours. Click for updated prices.
  • Lobby
    Jun 25 - Jul 3

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    8 nights
    4.0 star property
    8.2/10 - Very good (2,727 reviews)
    "Easy to get around location"
    Reviewed May 25, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,746
    €1,211
    per traveller
    found 7 hours ago
    Hotel Felix River North/Magnificent Mile
  • View from property
    Jun 25 - Jul 3

    The Talbott, Autograph Collection + Flight

    Downtown Chicago
    8 nights
    4.5 star property
    9.4/10 - Exceptional (117 reviews)
    "We thoroughly enjoyed our stay. The location was excellent, conveniently close to everything we needed. The room was spacious and spotless. The breakfast was fantastic, offering a wide variety of options to choose from. "
    Reviewed May 17, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    Save 100% on your flight
    €2,190
    €1,561
    per traveller
    found 8 hours ago
    The Talbott, Autograph Collection
  • 2 restaurants; breakfast, lunch, and dinner served
    Jun 25 - Jul 3

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    8 nights
    4.5 star property
    9.4/10 - Exceptional (3,725 reviews)
    "Super location, good crowd of staff and fellow travellers. Smells great!"
    Reviewed May 24, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,958
    €1,398
    per traveller
    found 7 hours ago
    LondonHouse Chicago, Curio Collection by Hilton
  • Exterior
    Jun 25 - Jul 3

    Hilton Garden Inn Chicago Downtown Riverwalk + Flight

    Downtown Chicago
    8 nights
    3.0 star property
    9.0/10 - Wonderful (1,937 reviews)
    "Front desk staff are cheerful and helpful. Checking was a breeze. On our 4 night stay our room was immaculately clean when we returned from our day's activities."
    Reviewed May 24, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    Save 100% on your flight
    €2,087
    €1,506
    per traveller
    found 7 hours ago
    Hilton Garden Inn Chicago Downtown Riverwalk
  • Studio, 2 Double Beds | Bathroom
    Jun 25 - Jul 3

    Sports Illustrated Resorts Chicago + Flight

    Downtown Chicago
    8 nights
    3.5 star property
    9.2/10 - Wonderful (1,395 reviews)
    "We paid for a studio city view and when we got to the hotel the placed on the 5th floor. No city view from the window. TV / remote did not work. Had to cast from my phone. When I tried showering there was only ice cold water. I called the front desk to ask if I’m doing something wrong they said they are trying to fix it. I booked this place for the convinces of getting ready for my graduation which backfired completely when we found out in the morning still no hot water. They said they would..."
    Reviewed May 21, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • Direct ORD - DUB • Direct
    €1,883
    €1,385
    per traveller
    found 8 hours ago
    Sports Illustrated Resorts 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
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

Top hotels in Wicker Park

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is €137 per night from 27 May to 28 May
€137
27 May - 28 May
includes taxes & fees
8/10 Very Good! (10,140 reviews)
"tiniest room i’ve ever stayed in and shower leaked all over the floor and"

Reviewed on 25 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is €269 per night from 16 Jun to 17 Jun
€269
16 Jun - 17 Jun
includes taxes & fees
9.4/10 Exceptional! (4,245 reviews)
"I wasn’t given a high floor or view like I asked a few months prior to the stay."

Reviewed on 25 May 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is €156 per night from 27 May to 28 May
€156
27 May - 28 May
includes taxes & fees
7.8/10 Good! (1,471 reviews)
"Staff was extremely helpful!"

Reviewed on 25 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,774 properties in Wicker Park
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.

Frequently asked questions

How much does a Wicker Park holiday package cost?
Choose from any combination of flights, hotels and car rentals, and you can be holidaying in Wicker Park from just . And the more you bundle, the more dollars you save. The getaway of your dreams has never been more affordable.
How do I get a cheap travel package to Wicker Park?
By bundling. Hotels, flights and rental cars — combine whatever you need into a Wicker Park holiday package to save a pile of cash. Score even bigger bargains when you include extras such as experiences or tours to your booking. But that's not the only good part. You have the freedom to tailor your trip your own way. We offer over 550 airlines and 1,000,000 properties across the globe, so that everyone has a chance to travel and live out those holiday dreams.
Where should I stay in Wicker Park?
Make sightseeing easier by staying near Wicker Park's biggest attractions. University of Illinois Chicago and United Centre are two of the best in the area.
What are the top hotels in Wicker Park?
If it's your very first time in Wicker Park, lock in a room at Wicker Park Inn or The Robey, Chicago, a Member of Design Hotels. Both hotels offer comfortable beds and are favourites with many travellers.
How far in advance should I book my Wicker Park holiday?
Your safest bet is to book early. Airlines typically release flights up to a year prior to departure, and this is a fantastic opportunity to score some rock-bottom prices. Boss just told you to use up your holiday time next week? That's fine too — Expedia are never short on fantastic bargains to send you off on the getaway of your dreams, at a price you can afford.
What does an Expedia Wicker Park travel package include?
Rental cars, flights and hotels, or any combination of them — it's your pick! Whether you're exploring Wicker Park with the entire family or travelling solo, there's a package to suit every style and budget. Once you've made your booking, why not add on a few tours as well?
What should I know before booking a Wicker Park travel package?
You can look forward to saving with an Expedia travel package. Combine your flights, rental cars and hotels and pick up exciting discounts. Hotels aren't your only option, however. Book with us and take your pick of beachside condos, chalets in the middle of mountains and even ranches and treehouses!
Can I choose my airline with a Wicker Park Expedia holiday package?
Yes, so take your pick! Expedia has access to more than 550 airlines around the world, so you can tailor your Wicker Park adventure according to your needs and budget.
If I'm not able to travel, can I cancel my Wicker Park holiday package?
If your holiday plans in Wicker Park have been upended, it's good to know that you can cancel or amend your booking. If you made your booking less than 24 hours ago, you may be able to get a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may impose a cancellation fee. For more details, visit our Customer Service Portal.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€23
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

€38
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

€39
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake 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.