West Englewood Vacation Packages

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

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Price found within the past 48 hours. Click for updated prices.
  • Breakfast and dinner served
    Jul 18 - Jul 21

    Omni Chicago Hotel + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,792 reviews)
    "Booked a room - got a suite! Enjoyed the extra space. A separate living room for watching TV or working at a desk. Staff at the hotel was very helpful. Enjoyed the breakfast too."
    Reviewed June 3, 2026
    Roundtrip • Hamilton (YHM) - Chicago (ORD)
    YHM - ORD • 1 stop ORD - YHM • 1 stop
    CA $1,723
    CA $1,307
    per traveller
    found 1 day ago
    Omni Chicago Hotel
  • Terrace/patio
    Aug 11 - Aug 15

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

    Downtown Chicago
    4 nights
    4.0 star property
    9.4/10 - Exceptional (2,527 reviews)
    "Loved the location. Fitness room was a little disappointing because it’s small and the there are only 2 peloton bikes, but one was out of commission."
    Reviewed June 4, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • Nonstop ORD - YUL • Nonstop
    CA $1,852
    CA $1,331
    per traveller
    found 1 day ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • Full-size fridge, microwave, oven, stovetop
    Aug 7 - Aug 10

    Level Chicago – Old Town + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.0/10 - Wonderful (488 reviews)
    "Very clean and loved the location and amenities with the store on the first floor was fantastic"
    Reviewed June 3, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $1,876
    CA $1,378
    per traveller
    found 1 day ago
    Level Chicago – Old Town
  • Lobby
    Aug 18 - Aug 21

    The Langham, Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,004 reviews)
    "Ask for a water view!"
    Reviewed May 31, 2026
    Roundtrip • Toronto (YYZ) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $2,216
    CA $1,653
    per traveller
    found 20 hours ago
    The Langham, Chicago
  • Terrace/patio
    Jul 21 - Jul 25

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    4 nights
    5.0 star property
    9.6/10 - Exceptional (1,884 reviews)
    "We love the pool, cleanliness in the room .Friendly staff"
    Reviewed June 6, 2026
    Roundtrip • Montreal (YUL) - Chicago (MDW)
    YUL - MDW • 1 stop MDW - YUL • 1 stop
    CA $2,871
    CA $2,205
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago

Where to stay in West Englewood

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

West Englewood 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 $202 per night from Jun 29 to Jun 30
CA $202
CA $241 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,194 reviews)
"The location is great for what we were in Chicago for. The property seemed a little dated and bathroom could have been cleaned better. Overall we had a good 2 night stay and for the price and location I would recommend."

Reviewed on Jun 7, 2026

Congress Plaza Hotel
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 $212 per night from Jun 28 to Jun 29
CA $212
CA $252 total
Jun 28 - Jun 29
includes taxes & fees
7.8/10 Good! (1,531 reviews)
"Had a pretty great stay. Everything was really nice. Only complaint was how slow the elevators were but I assume it’s bc of the age of the building. The towels in my room were brand spanking new so it did have a lot of fuzz. Overall though, this hotel was great and it’s in a really good location. ..."

Reviewed on Jun 7, 2026

The Chicago Hotel Collection - Magnificent Mile
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 $230 per night from Jun 29 to Jun 30
CA $230
CA $273 total
Jun 29 - Jun 30
includes taxes & fees
8.2/10 Very Good! (1,561 reviews)
"No water sold in the hotel. Instead they tried to upsell me in a package that I didn’t need. Think you need to change that policy. Our entire group of 4 rooms were disappointed."

Reviewed on Jun 7, 2026

The Chicago Hotel Collection Ambassador Gold Coast
See all 4,752 properties in West Englewood
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.
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Frequently asked questions

How much does a West Englewood vacation package cost?
Get ready to book, because a trip to West Englewood starts from just . When you bundle your hotels, flights and car rentals into a travel package, you'll enjoy the best prices.
How do I get a cheap travel package to West Englewood?
Our West Englewood vacation packages offer plenty of savings for the savvy explorer. For the best deal, simply combine your hotel, flights and tours into a handy package. But bargain prices are just the beginning of your next unforgettable adventure. When you book with Expedia, you'll have more than 550 air carriers and 1,000,000 hotel options throughout the world to select from. No matter your budget or style, there's a vacation package that's perfect for you.
Where should I stay in West Englewood?
You'll want to stay where the action is. Many visitors favor hotels around top sights, like Marquette Park, St. Bernard Hospital and Balzekas Museum of Lithuanian Culture.
How far in advance should I book my West Englewood vacation?
While prices change from time to time, we generally suggest booking your vacation as soon as possible. Many international fares can be compared on Expedia up to a year in advance. If you're booking late, you may still get lucky. Discount prices to West Englewood sometimes appear only weeks before departure.
What does an Expedia West Englewood travel package include?
With Expedia, you can choose a combination of flights, car rentals and hotels to create your ideal West Englewood travel package. Once you've made your booking, you can add on the fun stuff like sightseeing tours and activities. Remember, the more you bundle, the more deals you'll score!
What should I know before booking a West Englewood travel package?
You can save a tidy sum by bundling your airfares, hotels and rental cars. Once you've created your package, you can add on sightseeing tours or experiences. Your next awesome vacation is only a couple of clicks away.
Can I choose my airline with a West Englewood Expedia vacation package?
Yes, the choice is yours. We offer more than 550 airlines around the world, so you can tailor your West Englewood escape according to your travel needs.
If I'm not able to travel, can I cancel my West Englewood vacation package?
Plans can change suddenly, so yes, you can. You may be able to amend or cancel your West Englewood vacation package at no cost if you've booked in the last 24 hours. For bookings made more than 24 hours ago, you can still cancel or make changes, but your car rental company, airline or hotel may charge additional fees. Looking for more information? Take a look at our Customer Service Portal. We'll help make sure your trip goes off without a hitch.

Discover the most popular places to visit in West Englewood

Wrigley Field

Wrigley Field

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

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

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 $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $56
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.