Wicker Park Vacation Packages
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Top Holiday Package Deals in Wicker Park
Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare – Rosemont by IHG
CA $1,062
per person
Oct 2 - Oct 6
found 19 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,097 reviews)
Front desk staff were very friendly and helpful even though we didn't get to the hotel until after midnight because of flight delays.
Reviewed on Aug 10, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,569
per person
Oct 2 - Oct 6
found 19 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Breakfast lovely, with a lot of options that varied daily. I love the Riu hotels, and this one didn’t disappoint. Would definitely return.
Reviewed on Aug 10, 2026
Swissotel - Chicago
Downtown Chicago
CA $1,405
per person
Oct 2 - Oct 6
found 19 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9/10 Wonderful! (3,537 reviews)
We were in town for a family event. Had three rooms because of adult children. Everyone was friendly and helpful. Nice quiet location in downtown. Highly recommend.
Reviewed on Aug 10, 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
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.
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.
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.
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 the city at Washington Station or Monroe Station (Blue Line).
Wicker Park Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $146
CA $173 total
Sep 8 - Sep 9
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
CA $199
CA $237 total
Aug 30 - Aug 31
includes taxes & fees
8/10 Very good! (1,976 reviews)
"Great location for our stay, but the "double" beds seemed even tinier than doubles, the bathrooms are old and could use a refresh- drainage in the shower was an issue, and they wouldn't refresh the room in the middle of a 4 day stay- just dropped off new sheets and towels. Lobby is nice, and the ..."
Reviewed on Aug 10, 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
CA $315
CA $369 total
Sep 5 - Sep 6
includes taxes & fees
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 vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Wicker Park from just CA $1,062. 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 vacation 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 vacation 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 Center 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 favorites with many travelers.
How far in advance should I book my Wicker Park vacation?
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 vacation 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 traveling 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 vacation 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 vacation package?
If your vacation 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 theater 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 theater scene in this vibrant area.
Wood Street Gallery
You can spend time exploring the galleries in Wood Street Gallery during your travels in Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.
Flat Iron Building
You can learn about the history of Chicago when you stop by Flat Iron Building. Stroll along the lakeside or experience the acclaimed theater 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 theater scene in this vibrant area.
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 theater scene in this vibrant area.
Things to do
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.