Wicker Park Packages (Flight + Hotel)

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    Save up to ฿27,000 when you book a flight and hotel together*

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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

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

Top hotels in Wicker Park

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 ฿4,466 per night from 29 Jun to 30 Jun
฿4,466
฿5,310 total
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,237 reviews)
"First, this is a historic hotel, and visitors should be aware that the rooms reflect the historic vibe. If you want modern, you need to stay down the street at the Hilton. The rooms were very cute and clean, and the tiling in the bathroom was beautiful. The hotel has a prime location with easy walking ..."

Reviewed on 10 Jun 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
The price is ฿5,244 per night from 1 Jul to 2 Jul
฿5,244
฿6,235 total
1 Jul - 2 Jul
includes taxes & fees
7.8/10 Good! (1,551 reviews)
"Enjoyed our stay"

Reviewed on 10 Jun 2026

The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is ฿5,235 per night from 28 Jun to 29 Jun
฿5,235
฿5,967 total
28 Jun - 29 Jun
includes taxes & fees
8.8/10 Excellent! (2,644 reviews)
"The door to the restroom kept getting jammed and wouldn’t close properly. Our room also had no WiFi… the staff couldn’t figure out why it wasn’t working."

Reviewed on 10 Jun 2026

Hyatt Regency O'Hare Chicago
See all 4,663 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 . 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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

฿874
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago CityPASS: Admission to Top 5 Chicago Attractions

Chicago CityPASS®: Experience 5 must-see attractions

฿4,715
per adult
94% of travellers recommend
Chicago CityPASS®: Experience 5 must-see attractions
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

฿3,569
per adult
90% of travellers recommend
Chicago C3® by CityPASS®
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.