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.
Delta Hotels by Marriott Chicago Willowbrook

Delta Hotels by Marriott Chicago Willowbrook

3 out of 5
per person
Aug 28 - Sep 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.2/10 Very Good! (429 reviews)
The staff was very friendly. Fast check-in and check-out with no issues! Second time staying here and will stay again!

Reviewed on Jul. 24, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Nice hotel with a great breakfast buffet

Reviewed on Jul. 25, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Large rooms, excellent view and location

Reviewed on Jul. 24, 2025

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,986 reviews)
The line to get coffee at the cafe downstairs was always 12 people deep. The staff was not very fast…

Reviewed on Jul. 21, 2025

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,584 reviews)
Good building, a little misleading when “separate sitting area” is mentioned in the room, yet the room is still just 2 queen beds and a desk and bench all still in the same room. How is this separate if it’s in the same room? Walkable to downtown with access to everything. Clean enough

Reviewed on Jul. 25, 2025

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 showing a city

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

Wicker Park Hotel Deals

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 CA $183 per night from Aug 24 to Aug 25
CA $183
CA $215 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (8,964 reviews)
"The staff was very friendly and helpful"

Reviewed on Jul. 25, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
The price is CA $333 per night from Aug 22 to Aug 23
CA $333
CA $435 total
Aug 22 - Aug 23
includes taxes & fees
9/10 Wonderful! (2,087 reviews)
"The staff was friendly and welcoming, the room was bigger than expected, my only issue was the bathroom shower must of had a leak around the edges because when I got out there was water all over the bathroom floor and I know I closed that glass door to shower. It happening to my husband when he showered ..."

Reviewed on Jul. 22, 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $196 per night from Aug 24 to Aug 25
CA $196
CA $230 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (2,528 reviews)
"Convenient to the public transportation and nearby shopping. On-site restaurant was a good breakfast option for us before heading out for the day."

Reviewed on Jul. 24, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,646 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.
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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 $620. 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.

Things to do

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals

CA $55
per adult
100% of travellers recommend
Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals
Wicker Park Walking Tour History Trivia and Local Flavors

Wicker Park Walking Tour History Trivia and Local Flavors

CA $55
per adult
Wicker Park Walking Tour History Trivia and Local Flavors
River tour boat in Chicago

Architecture River Tour

CA $67
per adult
96% of travellers recommend
Architecture River Tour
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.