Wicker Park Holidays from £1,216

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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.
Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Price was £1,625, price is now £1,216 per person
£1,216
per person
11 Sept - 16 Sept
found 23 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,388 reviews)
We originally had room 2101 and the ac or mini fridge didn’t work so we were given another room 1601 and everything worked. Trip was great.

Reviewed on 9 Jul 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,035, price is now £1,325 per person
£1,325
per person
11 Sept - 16 Sept
found 23 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.

Reviewed on 9 Jul 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,852, price is now £1,238 per person
£1,238
per person
11 Sept - 16 Sept
found 23 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!

Reviewed on 8 Jul 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,890, price is now £1,386 per person
£1,386
per person
1 Oct - 6 Oct
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (512 reviews)
Front desk staff was super helpful and enthusiastic. Smooth check-in, and checkout.

Reviewed on 8 Jul 2026

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was £1,928, price is now £1,446 per person
£1,446
per person
11 Sept - 16 Sept
found 23 hours ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,251 reviews)
Viceroy staff were

Reviewed on 7 Jul 2026

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
A busy city street with tall buildings, a bus, and cars.

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

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is £137 per night from 27 Jul to 28 Jul
£137
27 Jul - 28 Jul
includes taxes & fees
8.2/10 Very good! (1,724 reviews)
"We were happy to be given a room before check in time, but the one we were given was dirty and not cleaned from the previous person. We were given another room which worked out fine. We enjoyed that it was historic but renovated for the most part. The downfall was that we could hear the neighbors ..."

Reviewed on 9 Jul 2026

The Chicago Hotel Collection Ambassador Gold Coast
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is £209 per night from 9 Aug to 10 Aug
£209
9 Aug - 10 Aug
includes taxes & fees
9.2/10 Wonderful! (1,894 reviews)
"It was an amazing hotel!"

Reviewed on 9 Jul 2026

Omni Chicago Hotel
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 £165 per night from 6 Aug to 7 Aug
£165
6 Aug - 7 Aug
includes taxes & fees
8/10 Very good! (10,217 reviews)
"Our stay was great, best was comfortable and room was clean."

Reviewed on 9 Jul 2026

Congress Plaza Hotel
See all 4,506 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 £1,216. 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.

Stay near popular Wicker Park attractions

The Den Theatre

After visiting The Den Theatre, make a plan to see the other sights and activities in Chicago. Experience the live music and theatre scene in this vibrant area.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£19
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£31
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture 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. Flight-inclusive packages are ATOL protected.