Wicker Park Holidays
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Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
€1,406
per person
17 Sept - 21 Sept
found 22 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
The property waa clean and spacious
Staff were very nice and helpful. The location was perfect a short walk or drive to alot of places ans the best of all was that
A Garrett's popcorn shop waa right across the street!
Reviewed on 11 Aug 2026
Silversmith Hotel Chicago Downtown
Downtown Chicago
€1,846
per person
6 Oct - 11 Oct
found 1 day ago
Return direct flight included
Tirana (TIA) to Chicago (ORD)
9.4/10 Exceptional! (2,311 reviews)
Booked this property for a one night stay,
We got the room almost a hour later.
And while talking to staff they felt that it’s usual.
Because of this we missed our booked River Architecture cruise and had to book it again for next day.
Rooms were not very clean either Carpet felt moist.
Location is great but Quality is not.
All in all it’s not worth the price which I was charged $500 for one night.
Reviewed on 10 Aug 2026
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
4 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.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Theatre District
While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).
Top hotels in Wicker Park
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
€118
8 Sept - 9 Sept
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
€147
31 Aug - 1 Sept
includes taxes & fees
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
€233
11 Sept - 12 Sept
includes taxes & fees
8.4/10 Very good! (2,388 reviews)
"Extremely well located and expensive, of course. The staff were well-trained. Very over-air conditioned. Decor straight out of the 70s?"
Reviewed on 11 Aug 2026
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 €974. 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.
Stay near popular Wicker Park attractions
The Den Theatre
After visiting The Den Theatre, make a plan to see the other sights and activities in Chicago. Experience the live music and theatre scene in this vibrant area.
The Chop Shop & 1st Ward
You can enjoy a show at The Chop Shop & 1st Ward during your trip to Chicago. Experience the live music and theatre scene in this vibrant area.
Flat Iron Building
You can learn about the history of Chicago with a visit to Flat Iron Building. Stroll along the lakeside or experience the acclaimed theatre scene in this vibrant area.
Bourbon On Division
Bourbon On Division is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the live music and theatre scene in this vibrant area.
Wood Street Gallery
You can spend time studying the exhibits at Wood Street Gallery during your travels in Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.
Monique Meloche Gallery
You can spend time browsing the exhibits at Monique Meloche Gallery during your travels in Chicago. Stroll along the lakeside or experience the fascinating museums in this vibrant area.
SWIG
After visiting SWIG, make a plan to see the other sights and activities in Chicago. Experience the live music and theatre scene in this vibrant area.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
€21
per adult
88% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.