Wicker Park Holidays

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Your Wicker Park Holiday

If it's time for a commercial retreat, our Wicker Park holiday packages are just what you need. Whether you're searching for nightlife, bars and pubs or cafes, this neighbourhood has something for every visitor. Wondering what to see and do during your trip to Wicker Park? Nearby attractions such as Wrigley Field, Willis Tower and John Hancock Centre are good places to start. Expedia can help you turn your ideal Wicker Park holiday into reality, whatever your travel plans or budget.

Price found within the past 48 hours. Click for updated prices.
  • Indoor wedding
    Jul 7 - Jul 12

    Swissotel - Chicago + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.0/10 - Wonderful (3,342 reviews)
    "The room was fantastic, the hotel bar was fantastic, the staff was fantastic. My only complaint is the restaurant closed at 9p on a Saturday. Overall four out of five experience"
    Reviewed May 25, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £1,126
    £767
    per traveller
    found 2 days ago
    Swissotel - Chicago
  • Smart TV
    Jul 7 - Jul 12

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.2/10 - Wonderful (488 reviews)
    "Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely."
    Reviewed May 22, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    Save 100% on your flight
    £1,339
    £890
    per traveller
    found 2 days ago
    Level Chicago Fulton Market
  • Terrace/patio
    Jul 7 - Jul 12

    Sable at Navy Pier Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.4/10 - Exceptional (2,511 reviews)
    "Walls are paper thin. We literally heard snoring all night from the room next to us. Also, the smell of cigarette smoke kept coming into our room. Rooms were nice and clean. The view was 🔥."
    Reviewed May 23, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £1,427
    £1,009
    per traveller
    found 2 days ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Executive lounge
    Jul 7 - Jul 12

    Fairmont Chicago at Millennium Park + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    8.8/10 - Excellent (2,167 reviews)
    "Perfect location to sight see Chicago. Staff were not friendly and when I asked a question felt like it was too much effort for them to respond in a professional helpful manner. Saying that the hotel was beautiful and the rooms were perfect. Great view."
    Reviewed May 24, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £1,113
    £810
    per traveller
    found 2 days ago
    Fairmont Chicago at Millennium Park
  • Lobby
    Jul 7 - Jul 12

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    8.2/10 - Very good (2,721 reviews)
    "Great location and helpful staff. Small rooms and public areas."
    Reviewed May 25, 2026
    Return • Dublin (DUB) - Chicago (ORD)
    DUB - ORD • 1 stop ORD - DUB • 1 stop
    £1,087
    £796
    per traveller
    found 2 days ago
    Hotel Felix River North/Magnificent Mile

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 £118 per night from 26 May to 27 May
£118
26 May - 27 May
includes taxes & fees
8/10 Very Good! (10,139 reviews)
"tiniest room i’ve ever stayed in and shower leaked all over the floor and"

Reviewed on 25 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is £233 per night from 16 Jun to 17 Jun
£233
16 Jun - 17 Jun
includes taxes & fees
9.4/10 Exceptional! (4,240 reviews)
"Solo traveler. Spacious king room. Double sink bathroom. The breakfast buffett was one of the best I've had. Convenient location to Michigan Ave and Riverwalk."

Reviewed on 25 May 2026

Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is £107 per night from 27 May to 28 May
£107
27 May - 28 May
includes taxes & fees
7.8/10 Good! (1,467 reviews)
"Complimentary breakfast was really nice."

Reviewed on 24 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,757 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Wicker Park travel package cost?
Go from looking to booking with our Wicker Park travel packages, which start from only . Pick the hotels and flights that suit your plans. Then, add on a few tours or activities to round off your unique getaway.
If I'm not able to travel, can I cancel my Wicker Park travel package?
We totally understand — life sometimes gets in the way of your plans. If you've locked in a Wicker Park travel package and need to cancel or change it, we can help. It's always worth browsing our Customer Service Portal first for information. But in general, if you've booked your package within 24 hours, you may be able to change your itinerary for free. If it's more than 24 hours, your airline, hotel or car rental company may impose a charge.
How do I get a cheap travel package to Wicker Park?
You'll save tons of cash if you bundle your hotels, flights and car rentals into a Wicker Park travel package. Sometimes cheap means fewer choices. But that's not the case with Expedia. We offer over 550 air carriers and 1,000,000 hotels across the globe, so you'll always have plenty of options to choose from. Want to save even more? Add some interesting activities to your package deal and unlock even more bargains! After all, travel is about more than just getting to your destination.
Does Expedia offer Book Now, Pay Later Wicker Park holidays?
Expedia has teamed up with online lender Klarna to make your next trip easier on your budget. Paying in instalments means you can spread the costs of your next big holiday, leaving you with more cash to play with while you're travelling. Klarna has several payment plans to choose from, so you're sure to find one that fits your budget. Take a look at these flexible payment options:

  • Pay monthly holidays: Klarna has convenient monthly payment plans that suit all budgets, so you can have that well-earned holiday now.
  • Pay in instalments holidays: Like the idea of paying down your holiday in multiple transactions? Then go for this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: Clicking the "book now" button is much easier with this payment option. Simply put down a small deposit on your escape and then start working on your travel itinerary.

Where should I stay in Wicker Park?
Most visitors to Wicker Park include both Millennium Park and Wrigley Field on their to-do lists. Why not go for a hotel within walking distance of these popular attractions?
What are the top hotels in Wicker Park?
Book a stay at Hyatt Regency Chicago. It's one of this neighbourhood's most popular hotels. Another well-known option in Wicker Park is The Godfrey Hotel Chicago.
How far in advance should I book my Wicker Park holiday?
Travellers are normally able to look up international airfares on Expedia within 12 months of the departure date. Booking last minute? With a bit of luck, it's still possible to purchase a cheap ticket only weeks before your journey.
What does an Expedia Wicker Park travel package include?
That depends on what you're looking for. If you're travelling solo, you might decide to combine flights and hotels. Bringing the whole crew to Wicker Park? A travel package that includes flights, hotels and rental cars might be a better fit. Expedia gives you the freedom to customize your travel package.
What should I know before booking a Wicker Park travel package?
Locking in all the parts of your holiday together is one of the easiest ways to save. Combine your car rentals, airfares and hotels into a convenient little package. But your options don't end at hotels. Expedia offers all sorts of properties, including holiday rentals like oceanfront condos and serviced residences. The list is almost endless!
Can I choose my airline with a Wicker Park Expedia travel package?
Definitely. Expedia has more than 550 partner airlines to select from around the world. With so many choices, finding the perfect carrier to take you to Wicker Park won't be difficult.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

£16
per child
98% of travellers recommend
Flyover in 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. Flight-inclusive packages are ATOL protected.