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

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Top Holiday Package Deals in Englewood

Price found within the past 48 hours. Click for updated prices.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Price was CA $1,874, price is now CA $1,171 per person
CA $1,171
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,129 reviews)
Great staff. Room was small. Good location.

Reviewed on Jun 17, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,999, price is now CA $1,337 per person
CA $1,337
per person
Sep 2 - Sep 6
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.

Reviewed on Jun 11, 2026

Great Wolf Lodge Illinois

Great Wolf Lodge Illinois

3 out of 5
Price was CA $2,088, price is now CA $1,422 per person
CA $1,422
per person
Aug 2 - Aug 6
found 16 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
8.6/10 Excellent! (1,003 reviews)
My family and I truly enjoyed our recent stay in the Junior Cabin Suite with a balcony. The accommodations provided everyone with plenty of personal space, and the room was both nice and clean. I especially want to commend Amar for his excellent customer service. He went above and beyond to ensure I was not double-charged for our rooms and made sure we had everything we needed throughout our stay. The entire staff was excellent, and we appreciated the flexible parking options. We would definitely recommend your property to others and look forward to returning very soon.

Reviewed on Jun 15, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,839, price is now CA $1,302 per person
CA $1,302
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,127 reviews)
We were celebrating an anniversary. We had a greay stay. It was close to all the shopping and restaurants, staff were great and helpful. We will be back again!

Reviewed on Jun 18, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,902, price is now CA $2,102 per person
CA $2,102
per person
Aug 3 - Aug 8
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (493 reviews)
If you drive, it’s very close to everything pretty much. It’s clean and nice to stay with family. Parking is a little expensive but that applies to most of Chicago area.

Reviewed on Jun 14, 2026

Where to stay in Englewood

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

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 $192 per night from Jun 29 to Jun 30
CA $192
CA $229 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,124 reviews)
"Great location for the hotel to be close where you want to go. Walking distance to the places we wanted to visits. We were there for 2026 Pokemongo Fest Chicago- Grant Park. So, it was an excellent location. Room had a view of the river/water. Room was very spacious for a standard double bed room ..."

Reviewed on Jun 18, 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 $193 per night from Jun 28 to Jun 29
CA $193
CA $229 total
Jun 28 - Jun 29
includes taxes & fees
7.8/10 Good! (1,591 reviews)
"Property was very outdated on the 8th floor. No coffee maker no water . The refrigerator was on the floor. No chair or couch just beds. Not worth the cost!"

Reviewed on Jun 18, 2026

The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $215 per night from Jul 5 to Jul 6
CA $215
CA $245 total
Jul 5 - Jul 6
includes taxes & fees
8.8/10 Excellent! (2,664 reviews)
"Hotel main trash service pickup was directly below my room window and was extremely loud when unloading and loading rolloff dumpsters at 4am. No way to sleep through the noise. Shuttle service was very good to and from the airport. Toilet clogged after one use with no plunger available. Remodeling ..."

Reviewed on Jun 17, 2026

Hyatt Regency O'Hare Chicago
See all 4,635 properties in 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 an Englewood vacation package cost?
Choose from any combination of car rentals, flights and hotels, and you can be vacationing in Englewood from just CA $1,171. And the more you bundle, the more cash you save. Your dream vacation has never been more affordable.
How do I get a cheap travel package to Englewood?
Combining your hotel and flight with Expedia won't just save you time — it'll save you a pretty penny too. An Englewood vacation package makes it a breeze to arrange the ideal trip. With more than 550 airlines across the world to pick from, finding convenient flights that suit your schedule won't be difficult. In addition to that, we've got over 1,000,000 hotel options globally to choose from. Talk about choice! No matter who you are, Expedia puts the world within your reach.
Where should I stay in Englewood?
With loads to explore in Englewood, it'd be convenient for you to book a hotel near its attractions. St. Bernard Hospital, Holy Cross Hospital and University of Illinois Mile Square Health Center are some interesting ones to put on your to-do list.
How far in advance should I book my Englewood vacation?
While prices change from time to time, we generally recommend booking your vacation as soon as possible. Many international fares are found on Expedia up to a year in advance. If circumstances have left you booking late, you may still get lucky. Discount prices to Englewood sometimes occur just weeks before departure.
What does an Expedia Englewood travel package include?
It all depends on what kind of trip you're contemplating. Englewood travel deals can include hotels, car rentals and flights. You can mix and match to find the package that suits your style and budget. You can also add on activities and experiences after you've booked to pick up even bigger discounts.
What should I know before booking an Englewood travel package?
Find deals to suit your budget with an Expedia package. Hotels, airfares, rental cars — we have everything you need to plan your escape. You'll save precious cash just by combining your bookings. Whether you're heading away on a ski trip or relaxing on a sunny beach, your dream vacation is just clicks away.
Can I choose my airline with an Englewood Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines worldwide. Our packages give you the freedom to pick from available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my Englewood vacation package?
Certainly, and we're here to help. You may be able to amend or cancel your Englewood vacation package at no cost if you booked in the last 24 hours. But you may be charged a fee by your airline, hotel or car rental company if you booked more than 24 hours ago. If your travel plans unexpectedly change, visit our Customer Service Portal for more information.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.