Wicker Park Holidays from NZ$2,045

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Top Holiday Package Deals in Wicker Park

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was NZ$2,596, price is now NZ$2,045 per person
NZ$2,045
per person
4 Nov - 9 Nov
found 18 hours ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.2/10 Wonderful! (2,120 reviews)
The hotel staff was great from the door men to front desk staff everyone was great.

Reviewed on 23 Sept 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was NZ$4,661, price is now NZ$3,143 per person
NZ$3,143
per person
4 Nov - 9 Nov
found 18 hours ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Worth every penny! Not much more than the "average" hotel when comparing all of the amenities. Will definitely stay here again!

Reviewed on 23 Sept 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was NZ$2,946, price is now NZ$2,122 per person
NZ$2,122
per person
4 Nov - 9 Nov
found 18 hours ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9/10 Wonderful! (1,004 reviews)
The room was perfect and the front staff were exceptional. Our stay was amazing!

Reviewed on 21 Sept 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was NZ$3,179, price is now NZ$2,500 per person
NZ$2,500
per person
4 Nov - 9 Nov
found 18 hours ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.4/10 Exceptional! (3,344 reviews)
Close to the riverwalk

Reviewed on 23 Sept 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was NZ$2,963, price is now NZ$2,347 per person
NZ$2,347
per person
4 Nov - 9 Nov
found 18 hours ago
Return flight included
Christchurch (CHC) to Chicago (ORD)
9.4/10 Exceptional! (2,142 reviews)
Great view and a great staff!

Reviewed on 22 Sept 2025

Our guide on 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 featuring 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

Our pick of the best 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
7.8/10 Good! (9,228 reviews)
"Hotel is older, but very well maintained."

Reviewed on 19 Sept 2025

Get rates
Congress Plaza Hotel
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 NZ$321 per night from 20 Oct to 21 Oct
NZ$321
20 Oct - 21 Oct
includes taxes & fees
8.8/10 Excellent! (2,901 reviews)
"Great location, close to different restaurants and coffee shops. Sadly the pool was closed when I was there but it looked like the property was very well maintained. Staff was so nice upon check in. Our room was nice and comfortable! Enjoyed my stay and will be back!!"

Reviewed on 19 Sept 2025

Hilton Chicago/Magnificent Mile Suites
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is NZ$360 per night from 2 Oct to 3 Oct
NZ$360
2 Oct - 3 Oct
includes taxes & fees
8.4/10 Very Good! (3,934 reviews)
"It was walking distance to Michigan Ave"

Reviewed on 21 Sept 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,585 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 holiday package cost?
Choose from any combination of flights, hotels and car rentals, and you can be holidaying in Wicker Park from just NZ$2,045. 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 holiday 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 holiday 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 Centre 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 favourites with many travellers.
How far in advance should I book my Wicker Park holiday?
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 holiday 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 travelling 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 holiday 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 holiday package?
If your holiday 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.

Activities

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

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

NZ$68
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

NZ$68
per adult
Wicker Park Walking Tour History Trivia and Local Flavors
Historic Homes and Cottages of Wicker Park Walking Tour

Historic Homes and Cottages of Wicker Park Walking Tour

NZ$76
per adult
Historic Homes and Cottages of Wicker Park Walking 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.