Wicker Park Holidays from AU$3,287
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Your Wicker Park Holiday
Lock in a holiday 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 neighbourhood, 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 Centre and Humboldt Park. No matter your travel goals or the size of your budget, booking your dream Wicker Park holiday has never been easier with Expedia.
Top Holiday Package Deals in Wicker Park
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
AU$3,287
per person
27 Dec - 3 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
The first room I checked in to had the door not flushly closing, and looked like someone had pried their way into the room.
I checked in at 2:30am after driving from the Green Bay Packers football game in Green Bay, and they insisted that I check out at 11am.
After two or three calls, they managed to delay it to 12:30pm.
They want a $100 an hour for every hour you stay in the room after 11am and they very aggressively enforce it.
I did not pay this amount and won't be staying at this hotel again and recommend that they change their customer service approach or clients will be choosing other hotels.
Reviewed on 21 Oct 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
AU$4,794
per person
27 Dec - 3 Jan
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Our stay was fabulous! Curtis, who checked us in (and out), was so helpful with food recommendations and like all staff we encountered, so very nice! Room was impeccably clean and quiet with amazing views! Can’t wait til our next stay
Reviewed on 20 Oct 2026
Our guide on 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.
Magnificent Mile
A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.
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.
The Loop
Striking architecture, urban park space and countless entertainment options all make The Loop one of the most memorable spots in the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Our pick of the best Wicker Park Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
AU$182
10 Nov - 11 Nov
includes taxes & fees
8/10 Very good! (10,176 reviews)
"The room I stayed in 1270 was terrible maintained. It was clean but shower seemed to have be poorly repaired too many times, toilet was loose and a bit crooked, the door nob on the bathroom door coming off, door on the dresser also crooked and tiles on the bathroom floor broken. The hotel does not ..."
Reviewed on 21 Oct 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
AU$205
11 Nov - 12 Nov
includes taxes & fees
8/10 Very good! (2,545 reviews)
"needs a major update. elevator is so tiny and there are chunks out of the wall covered by paint."
Reviewed on 21 Oct 2026
River Hotel
75 East Wacker Drive Chicago IL
AU$259
1 Nov - 2 Nov
includes taxes & fees
8.8/10 Excellent! (5,559 reviews)
"Very clean hotel, comfy bed & pillows. Water station was a plus. Great view of the river."
Reviewed on 20 Oct 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 AU$3,287. 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.
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.
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 entertainment choices.
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.
Activities
Skydeck Chicago at Willis Tower
AU$59
per adult
88% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.