Englewood 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.
  • Lobby
    Aug 6 - Aug 9

    JW Marriott Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.2/10 - Wonderful (1,003 reviews)
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,372
    CA $950
    per traveller
    found 1 day ago
    JW Marriott Chicago
  • Full-size fridge, microwave, oven, stovetop
    Jul 22 - Jul 25

    Level Chicago – Old Town + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    9.0/10 - Wonderful (483 reviews)
    "Nice and big"
    Reviewed May 24, 2026
    Roundtrip • Toronto (YTZ) - Chicago (MDW)
    YTZ - MDW • Nonstop MDW - YTZ • Nonstop
    CA $1,736
    CA $1,196
    per traveller
    found 1 day ago
    Level Chicago – Old Town
  • Dinner served
    Jul 16 - Jul 20

    Kimpton Gray Hotel by IHG + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (1,000 reviews)
    "Great hotel. Loved the lobby and our room. Would definitely stay here again."
    Reviewed May 19, 2026
    Roundtrip • Toronto (YTZ) - Chicago (MDW)
    YTZ - MDW • Nonstop MDW - YTZ • Nonstop
    CA $1,704
    CA $1,176
    per traveller
    found 1 day ago
    Kimpton Gray Hotel by IHG
  • Lobby lounge
    Aug 4 - Aug 9

    Le Méridien Essex Chicago + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    8.8/10 - Excellent (1,004 reviews)
    "False claim about the view. There is no view"
    Reviewed May 26, 2026
    Roundtrip • Toronto (YTZ) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,623
    CA $1,129
    per traveller
    found 1 day ago
    Le Méridien Essex Chicago
  • Seasonal outdoor pool, sun loungers
    Jul 16 - Jul 20

    Viceroy Chicago + Flight

    Downtown Chicago
    4 nights
    4.5 star property
    9.4/10 - Exceptional (1,230 reviews)
    "I don’t think I have ever encountered a more polite, charming, and informed staff. As someone who has worked in the service industry I assume that your training program does an excellent job. The hotel is beautiful and well maintained. We’ll be back."
    Reviewed May 25, 2026
    Roundtrip • Toronto (YTZ) - Chicago (MDW)
    YTZ - MDW • Nonstop MDW - YTZ • Nonstop
    CA $2,215
    CA $1,542
    per traveller
    found 1 day ago
    Viceroy Chicago

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
The price is CA $281 per night from Jun 3 to Jun 4
CA $281
CA $334 total
Jun 3 - Jun 4
includes taxes & fees
8/10 Very Good! (10,148 reviews)
"Hotel is pretty "okay" if you are going for business, but our experience was not nice. The Air Conditioner wasn't working on a 65-80 degree outside, I told the front desk if they can help or make a room change but the solution was to give me a floor fan, not the type of help I was hoping and did ..."

Reviewed on May 27, 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
The price is CA $330 per night from Jun 16 to Jun 17
CA $330
CA $432 total
Jun 16 - Jun 17
includes taxes & fees
9.4/10 Exceptional! (4,265 reviews)
"Staff was super friendly. Rooftop bar is awesome. The breakfast was fantastic. This may sound weird, but the toilet seats had abnormally large openings."

Reviewed on May 27, 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
The price is CA $263 per night from Jun 16 to Jun 17
CA $263
CA $312 total
Jun 16 - Jun 17
includes taxes & fees
7.8/10 Good! (1,480 reviews)
"Just parking"

Reviewed on May 27, 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,719 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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 . 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.

Discover the most popular places to visit in 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
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue

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.