West Englewood Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to NZ$2,400 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.
  • Executive lounge
    Aug 16 - Aug 22

    Fairmont Chicago at Millennium Park + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    8.8/10 - Excellent (2,170 reviews)
    "Amazing view and clean room"
    Reviewed May 25, 2026
    Return • Christchurch (CHC) - Chicago (ORD)
    CHC - ORD • 2 stops ORD - CHC • 2 stops
    NZ$4,157
    NZ$3,359
    per traveller
    found 6 hours ago
    Fairmont Chicago at Millennium Park
  • Indoor wedding
    Aug 16 - Aug 22

    Swissotel - Chicago + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.0/10 - Wonderful (3,348 reviews)
    "Excellent location, walk to all major attractions. Friendly staff. Hotel room was very clean and comfortable. Price was pretty reasonable"
    Reviewed May 26, 2026
    Return • Christchurch (CHC) - Chicago (ORD)
    CHC - ORD • 2 stops ORD - CHC • 2 stops
    NZ$4,443
    NZ$3,396
    per traveller
    found 6 hours ago
    Swissotel - Chicago
  • Smart TV
    Aug 16 - Aug 22

    Level Chicago Fulton Market + Flight

    Downtown Chicago
    5 nights
    4.0 star property
    9.2/10 - Wonderful (488 reviews)
    "Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely."
    Reviewed May 22, 2026
    Return • Christchurch (CHC) - Chicago (ORD)
    CHC - ORD • 2 stops ORD - CHC • 2 stops
    NZ$4,329
    NZ$3,387
    per traveller
    found 6 hours ago
    Level Chicago Fulton Market
  • Terrace/patio
    Aug 16 - Aug 22

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

    Downtown Chicago
    5 nights
    4.0 star property
    9.4/10 - Exceptional (2,515 reviews)
    "Great views of the lake, staff very helpful the rooms were clean and comfortable. Would stay there again!"
    Reviewed May 26, 2026
    Return • Christchurch (CHC) - Chicago (ORD)
    CHC - ORD • 2 stops ORD - CHC • 2 stops
    NZ$4,569
    NZ$3,634
    per traveller
    found 6 hours ago
    Sable at Navy Pier Chicago, Curio Collection by Hilton
  • 2 restaurants; breakfast, lunch, and dinner served
    Aug 16 - Aug 22

    LondonHouse Chicago, Curio Collection by Hilton + Flight

    Downtown Chicago
    5 nights
    4.5 star property
    9.4/10 - Exceptional (3,727 reviews)
    "Excellent location! Great views from our room."
    Reviewed May 25, 2026
    Return • Christchurch (CHC) - Chicago (ORD)
    CHC - ORD • 2 stops ORD - CHC • 2 stops
    NZ$4,169
    NZ$3,369
    per traveller
    found 6 hours ago
    LondonHouse Chicago, Curio Collection by Hilton

Our guide on 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

Our pick of the best West Englewood Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is NZ$270 per night from 27 May to 28 May
NZ$270
27 May - 28 May
includes taxes & fees
8/10 Very Good! (10,141 reviews)
"Everything was perfect. Great customer service."

Reviewed on 25 May 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 NZ$533 per night from 16 June to 17 June
NZ$533
16 June - 17 June
includes taxes & fees
9.4/10 Exceptional! (4,251 reviews)
"This hotel is amazing, Great location, super clean and stuff was kind, informative and very respectful! The breakfast was well organized considering the amount people served! Not a missing items at any moment! The rooftop bar was very pleasant place to sit and chill. Strongly recommended!!!"

Reviewed on 26 May 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 NZ$385 per night from 3 June to 4 June
NZ$385
3 June - 4 June
includes taxes & fees
7.8/10 Good! (1,476 reviews)
"The room was clean and staffs were approachable. Hotel is close to nearby restaurants and shops."

Reviewed on 25 May 2026

The Chicago Hotel Collection - Magnificent Mile
See all 4,781 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.

Frequently asked questions

How much does a West Englewood holiday 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 holiday 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 holiday 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 holiday?
While prices change from time to time, we generally suggest booking your holiday 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 holiday is only a couple of clicks away.
If I'm not able to travel, can I cancel my West Englewood holiday package?
Plans can change suddenly, so yes, you can. You may be able to amend or cancel your West Englewood holiday 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

A big piece of Chicago's soul, an ancient stadium that keeps alive the quirky, edgy madness of baseball.

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

One of Chicago’s most popular attractions, especially on a hot day, with its fun fair, boats, circus and theatre.

Navy Pier

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

NZ$45
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

NZ$74
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

NZ$77
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
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.