Wicker Park Vacations from ￥68,141

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    Save up to ￥45,448 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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The Latest Wicker Park Vacation Packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Chicago Schaumburg

DoubleTree by Hilton Chicago Schaumburg

4 out of 5
Price was ￥82,497, price is now ￥68,141 per person
￥68,141
per person
Jan 5 - Jan 8
found 23 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Chicago (ORD)
7.2/10 Good! (1,003 reviews)
Clean rooms, helpful staff & good breakfast

Reviewed on Dec 3, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was ￥264,560, price is now ￥189,924 per person
￥189,924
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Yes room was clean and orderly with everything in place. Front desk and dining staff were professional and thoughtful. Music in restaurant was a bit high for volume, more relaxing type of music would be nice. Food was good and happy hour specials were nice. enjoyed our stay.

Reviewed on Nov 26, 2025

Chicago luxury home suites

Chicago luxury home suites

2 out of 5
Downtown Chicago
Save 100% on your flight
Price was ￥475,074, price is now ￥349,831 per person
￥349,831
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
10/10 Exceptional! (1 review)
Great service and communication throughout my entire stay. Very clean and easy to access to everything that i needed. Even though it was a short stay but had a comfortable and pleasant stay. Everything was available for me before i arrived. Thank you really. Great job.

Reviewed on Nov 26, 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
Price was ￥135,572, price is now ￥106,626 per person
￥106,626
per person
Jan 5 - Jan 8
found 23 hours ago
Roundtrip non-stop flight included
Hartford (BDL) to Chicago (ORD)
8.2/10 Very Good! (2,158 reviews)
Slept so good I missed my flight

Reviewed on Dec 4, 2025

Hotel Chicago Downtown, Autograph Collection by Marriott

Hotel Chicago Downtown, Autograph Collection by Marriott

4 out of 5
Downtown Chicago
Price was ￥178,086, price is now ￥147,206 per person
￥147,206
per person
Feb 19 - Feb 23
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (1,003 reviews)
Everything was great.

Reviewed on Dec 5, 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

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥14,629 per night from Dec 18 to Dec 19
￥14,629
￥17,174 total
Dec 18 - Dec 19
includes taxes & fees
8.4/10 Very Good! (5,348 reviews)
Great location, beautiful property, excellent breakfast, spacious rooms.

Reviewed on Dec 3, 2025

Embassy Suites by Hilton Chicago Downtown River North
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 ￥16,282 per night from Dec 14 to Dec 15
￥16,282
￥19,114 total
Dec 14 - Dec 15
includes taxes & fees
8.8/10 Excellent! (3,430 reviews)
Great

Reviewed on Dec 4, 2025

Hilton Chicago/Magnificent Mile Suites
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥15,901 per night from Dec 28 to Dec 29
￥15,901
￥22,544 total
Dec 28 - Dec 29
includes taxes & fees
8.4/10 Very Good! (2,128 reviews)
The room was beautiful, the hotel was decorated for Christmas. Clean, felt safe, friendly staff.

Reviewed on Dec 4, 2025

Palmer House a Hilton Hotel
See all 4,826 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 ￥68,141. 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

Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

￥7,083
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,866
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

￥6,296
per adult
92% of travellers recommend
Art Institute of Chicago
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.