Wicker Park Vacations from ￥187,492

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The Latest Wicker Park Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
Aug 31 - Sep 3
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,785 reviews)
Hard to sleep at night due to noise.

Reviewed on Jul 20, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Aug 31 - Sep 3
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Lovely hotel in a great area close to everything. But so noisy at night- people seem to like racing in the streets - outside our window.

Reviewed on Jul 20, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
per person
Aug 31 - Sep 3
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9/10 Wonderful! (1,000 reviews)
I loved this hotel. It was absolutely beautiful!

Reviewed on Jul 17, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
Aug 31 - Sep 3
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,115 reviews)
Nice hotel. Good location near train station. Lots of food options at and around the hotel. Would stay again.

Reviewed on Jul 20, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Aug 31 - Sep 3
found 1 hour ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
Enjoyed the stay. Rooftop bar is great!

Reviewed on Jul 20, 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
The price is ￥19,989 per night from Aug 18 to Aug 19
￥19,989
￥23,467 total
Aug 18 - Aug 19
includes taxes & fees
7.8/10 Good! (8,900 reviews)
"It was very centralized. The history made it even more interesting. It’s convenient because it’s centralized."

Reviewed on Jul 20, 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
Fully refundable
The price is ￥37,054 per night from Jul 24 to Jul 25
￥37,054
￥48,261 total
Jul 24 - Jul 25
includes taxes & fees
9/10 Wonderful! (2,071 reviews)
"Great location!"

Reviewed on Jul 19, 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 ￥21,377 per night from Aug 17 to Aug 18
￥21,377
￥25,093 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (2,495 reviews)
"Loved it!"

Reviewed on Jul 20, 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.

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 ￥187,492. 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

￥5,864
per adult
100% of travellers recommend
Offbeat Street Art Tour of Chicago: Urban Graffiti, Art, and Murals
Historic Homes and Cottages of Wicker Park Walking Tour

Historic Homes and Cottages of Wicker Park Walking Tour

￥6,597
per adult
Historic Homes and Cottages of Wicker Park Walking Tour
River tour boat in Chicago

Architecture River Tour

￥7,149
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.