Bucktown Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

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

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • 4 restaurants; breakfast, lunch, dinner, and brunch served
    Aug 10 - Aug 15

    Chicago Athletic Association, a Hyatt Hotel + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.0/10 - Wonderful (1,004 reviews)
    "S"
    Reviewed May 19, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • Nonstop ORD - YUL • Nonstop
    CA $1,769
    CA $1,257
    per traveller
    found 5 hours ago
    Chicago Athletic Association, a Hyatt Hotel
  • Full-size fridge, microwave, oven, stovetop
    Aug 2 - Aug 7

    Level Chicago – Old Town + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.0/10 - Wonderful (481 reviews)
    "Nice and big"
    Reviewed May 24, 2026
    Roundtrip • Hamilton (YHM) - Chicago (ORD)
    YHM - ORD • 1 stop ORD - YYZ • 1 stop
    CA $2,232
    CA $1,411
    per traveller
    found 1 day ago
    Level Chicago – Old Town
  • Terrace/patio
    Jul 31 - Aug 5

    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
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • Nonstop ORD - YUL • Nonstop
    CA $3,275
    CA $2,074
    per traveller
    found 10 hours ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • 2 restaurants; breakfast, lunch, and dinner served
    Jul 31 - Aug 5

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (3,725 reviews)
    "Super location, good crowd of staff and fellow travellers. Smells great!"
    Reviewed May 24, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • Nonstop ORD - YUL • Nonstop
    CA $2,989
    CA $1,971
    per traveller
    found 10 hours ago
    LondonHouse Chicago, Curio Collection by Hilton
  • Meeting facility
    Jul 22 - Jul 25

    Thompson Chicago, by Hyatt + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,367 reviews)
    "Excellent hotel and close to restaurants and shopping. Very clean."
    Reviewed May 24, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $4,233
    CA $3,009
    per traveller
    found 1 day ago
    Thompson Chicago, by Hyatt

Where to stay in Bucktown

Find the best Bucktown areas and neighborhoods for the activities you enjoy most. Learn more about Bucktown
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

Bucktown Hotel Deals

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 CA $185 per night from May 26 to May 27
CA $185
CA $219 total
May 26 - May 27
includes taxes & fees
8/10 Very Good! (10,138 reviews)
"Good"

Reviewed on May 25, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $287 per night from May 26 to May 27
CA $287
CA $381 total
May 26 - May 27
includes taxes & fees
9.4/10 Exceptional! (4,237 reviews)
"Best hotel breakfast buffet I’ve ever experienced, so many options."

Reviewed on May 25, 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 CA $210 per night from May 27 to May 28
CA $210
CA $250 total
May 27 - May 28
includes taxes & fees
7.8/10 Good! (1,467 reviews)
"Complimentary breakfast was really nice."

Reviewed on May 24, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,758 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
Beach Vacations
Family Vacations
Family Vacations

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 . 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.

Discover the most popular places to visit in Bucktown

Wrigley Field

Wrigley Field

4.5/5(159 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

4.5/5(3 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes
Navy Pier

Navy Pier

4.5/5(460 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $31
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.