Bucktown Holidays

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Where to stay in Bucktown

Find the best Bucktown areas and neighborhoods for the activities you enjoy most. Learn more about Bucktown
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 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.

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A river with yellow boats, a bridge, and tall buildings.

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

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A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

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A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

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A nighttime cityscape with fireworks over a body of water, a Ferris wheel, and illuminated buildings.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).

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Top hotels in Bucktown

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
S$161
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,294 reviews)
"I enjoyed my stay at the Congress Plaza. I had a room on the 11th floor with a terrific view of the lake. One problem: I stayed for two days and no housekeepers ever showed up to clean the room."

Reviewed on 13 Aug, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
S$218
31 Aug - 1 Sept
includes taxes & fees
8/10 Very good! (1,979 reviews)
"When I arrived, the staff was unfriendly when I went upstairs to my room the elevator and the carpets in the hallway were pretty dirty. My room was a mess had to ask for clean sheets because mine had sweat marks on them there was leftover orange juice in the room the bathroom also was a mass had ..."

Reviewed on 13 Aug, 2026

The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
S$258
16 Aug - 17 Aug
includes taxes & fees
8.8/10 Excellent! (5,373 reviews)
"They should do a better job in cleaning the room. The table and ledges are so dusty"

Reviewed on 13 Aug, 2026

River Hotel
See all 4,576 properties in Bucktown
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 Bucktown holiday package cost?
Choose from any combination of hotels, flights and car rentals, and you can be holidaying in Bucktown from just . And the more you bundle, the more you save. Your dream holiday has never been more affordable.
How do I get a cheap travel package to Bucktown?
Secure flights that suit your busy schedule, add a hotel room to your booking and watch how much you save with a Bucktown holiday package. It's as easy as that! From flights and hotels to rental cars and tours, Expedia makes travelling cheap and easy. And with over 550 airlines and 1,000,000 hotel options globally to select from, you'll never be short of choice.
Where should I stay in Bucktown?
A journey to Bucktown isn't over until you've seen Wrigley Field and Lincoln Park Zoo. Look for somewhere to stay close by so you can easily access these awesome tourist attractions.
What are the top hotels in Bucktown?
If this will be your first time in Bucktown, secure a room at The Hotel at Midtown or Ray's Bucktown B&B. Both offer comfortable beds and are favourites with many savvy travellers.
How far in advance should I book my Bucktown holiday?
The earlier you book, the better. Airlines usually release flights up to a year prior to departure, and this is when you can pick up some of the cheapest prices. Boss just told you to use up your holiday time next month? No need to worry. Expedia are never short of fantastic deals to whisk you away on the getaway of your dreams, at a price you can afford.
What does an Expedia Bucktown travel package include?
That depends on you. You can choose from a variety of Bucktown packages, such as a hotel, rental car and flight. You can also book a flight and a hotel, or a rental car with a flight. Once you've made your booking, you can add on the fun stuff like activities and tours. Whatever your ideal Bucktown break looks like, get ready to save!
What should I know before booking a Bucktown travel package?
Locking in all the parts of your trip together is an excellent way to save. Combine your car rentals, airfares and hotels into a neat little package. But hotels aren't your only option. Expedia offers all sorts of properties, including holiday rentals like mountain cabins and short-term homes. The list goes on!
Can I choose my airline with a Bucktown Expedia holiday package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines globally. Our packages give you the flexibility to take your pick of available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Bucktown holiday package?
You can cancel your Bucktown booking if your plans have changed. Whether you'll be charged a fee or not depends on your hotel, airline or car rental company. It may be possible to cancel or change your booking free of charge if you booked in the last 24 hours. Visit our Customer Service Portal to find out more.

Stay near popular Bucktown attractions

Riverfront Plaza

Explore the great outdoors at Riverfront Plaza, a lovely green space in Chicago. Discover the festivals and churches in this walkable area.
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Gorilla Tango Theatre

You can make plans for a show at Gorilla Tango Theatre during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.
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Holstein Park Public Pool

After visiting Holstein Park Public Pool, make a plan to see the other sights and activities in Chicago. Discover the festivals and churches in this walkable area.
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Holstein Park

You can take time to visit Holstein Park during your travels to Chicago. Discover the festivals and churches in this walkable area.
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Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

S$35
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

S$32
per adult
90% 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

S$52
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.