Bucktown Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*

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Top Holiday Package Deals in Bucktown

Price found within the past 48 hours. Click for updated prices.
Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $987, price is now CA $770 per person
CA $770
per person
Aug 16 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Clean rooms, nice pool, location great

Reviewed on Jul 12, 2026

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 CA $1,595, price is now CA $1,178 per person
CA $1,178
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,566 reviews)
Booked this stay for my husband Birthday. Wanted to make sure he enjoyed himself as well as me. I spent over $800 for the corner room, check in is at 4pm and we arrived about 430ish. Got to the room and the Amenities I purchased wasn’t there which was $100(they stated it would be at 4pm) which is why I want to arrive later. I noticed that the bed sheets were ripped, small stains on the couch in front of bed and the seat in the corner by the window that creeped me out. So we left and via Hilton app I contacted the Hotel to find out why my paid Amenities wasn’t there and they sat them in there while we were gone to dinner. We got back and the chocolate covered strawberries were melted. The best part about the stay was the firework show. My husband and I enjoyed ourselves as best we could after noticing these issues it was disgusting seeing the stains and the ripped sheets especially paying what was over $1000 for one night

Reviewed on Jul 13, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,055, price is now CA $806 per person
CA $806
per person
Aug 17 - Aug 19
found 1 day ago
Roundtrip flight included
Buffalo (BUF) 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 Jul 9, 2026

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt

4.5 out of 5
Downtown Chicago
Price was CA $1,494, price is now CA $1,168 per person
CA $1,168
per person
Sep 12 - Sep 15
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,388 reviews)
Beautiful hotel with nice city views. Friendly staff. So many hidden fees, doubled the cost.

Reviewed on Jul 12, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $989, price is now CA $775 per person
CA $775
per person
Aug 16 - Aug 18
found 1 day ago
Roundtrip non-stop flight included
Buffalo (BUF) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
The check in was seamless. Lobby spotless. Room was very clean and tidy. Rooftop area was super.

Reviewed on Jul 12, 2026

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

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

Bucktown Hotel Deals

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 CA $218 per night from Jul 27 to Jul 28
CA $218
CA $259 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very good! (1,740 reviews)
"This place will charge you a resort fee that doubles the cost of your stay. They also won’t communicate that to you or give you any receipts. Don’t stay here."

Reviewed on Jul 12, 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 CA $310 per night from Aug 10 to Aug 11
CA $310
CA $416 total
Aug 10 - Aug 11
includes taxes & fees
9.2/10 Wonderful! (1,914 reviews)
"Main area was nice. Hotel room was outdated"

Reviewed on Jul 13, 2026

Omni Chicago Hotel
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $324 per night from Aug 9 to Aug 10
CA $324
CA $380 total
Aug 9 - Aug 10
includes taxes & fees
8.4/10 Very good! (2,349 reviews)
"Great place to stay to catch a flight the next morning"

Reviewed on Jul 13, 2026

Hilton Chicago O'Hare Airport
See all 4,502 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations
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Frequently asked questions

How much does a Bucktown vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Bucktown from just CA $770. And the more you bundle, the more you save. Your dream vacation 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 vacation package. It's as easy as that! From flights and hotels to rental cars and tours, Expedia makes traveling 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 favorites with many savvy travelers.
How far in advance should I book my Bucktown vacation?
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 vacation 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 vacation rentals like mountain cabins and short-term homes. The list goes on!
Can I choose my airline with a Bucktown Expedia vacation 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 vacation 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

After visiting Riverfront Plaza, make a plan to see the other sights and activities in Chicago. Discover the festivals and churches in this walkable area.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $64
per adult
94% of travellers recommend
Wendella's Lake and 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.