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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Sep 23 - Sep 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
The hotel was nice, staff were friendly and the overall stay was excellent and convenient to walk.

Reviewed on Jul. 28, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (324 reviews)
Finding a park is hard and the process of getting a room is very tedious but still very beautiful I’ve been twice

Reviewed on Jul. 29, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on Jul. 22, 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
It was a great location , close to downtown core.

Reviewed on Jul. 30, 2025

The Wade

The Wade

4.5 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (1,066 reviews)
Deceiving marketing! When I booked I thought breakfast was included. It wasn’t

Reviewed on Jul. 29, 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 $185 per night from Aug 18 to Aug 19
CA $185
CA $217 total
Aug 18 - Aug 19
includes taxes & fees
7.8/10 Good! (8,994 reviews)
"The time of lake was awesome"

Reviewed on Jul. 27, 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 CA $315 per night from Aug 17 to Aug 18
CA $315
CA $414 total
Aug 17 - Aug 18
includes taxes & fees
9/10 Wonderful! (2,125 reviews)
"My two small daughters, 10 and under, and I were on a girls' trip to Chicago and stayed here. They were in awe of how friendly all the guests at the hotel were! Everyone was willing to share a fun fact of the city or just to welcome us. I also appreciated how easy it was to get to places, whether ..."

Reviewed on Jul. 29, 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 $198 per night from Aug 17 to Aug 18
CA $198
CA $232 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (2,557 reviews)
"Please diversify food options and open pool. Delayed check in but otherwise great property good staff."

Reviewed on Jul. 28, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,693 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
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Family Vacations

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 $713. 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.