Englewood Holidays

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    Save up to S$1,300 when you book a flight and hotel together*

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Price found within the past 48 hours. Click for updated prices.
Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

Downtown Chicago
S$613
per person
21 Nov - 23 Nov
found 17 hours ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.6/10 Excellent! (2,274 reviews)
The hotel was great and we chose this location because of all of the nearby shops and food options. The only real downside was we realized its very close to a fire station so there were sirens going off super often. Was very difficult to get used to that when it isnt our norm. Other than that, this was a good experience!

Reviewed on 10 Oct, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
Save 100% on your flight
S$1,059
per person
21 Nov - 23 Nov
found 17 hours ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
The Emily Hotel

The Emily Hotel

Downtown Chicago
S$754
per person
21 Nov - 23 Nov
found 17 hours ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (1,347 reviews)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
S$725
per person
21 Nov - 23 Nov
found 17 hours ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
S$739
per person
21 Nov - 23 Nov
found 17 hours ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.2/10 Wonderful! (532 reviews)
Great location, very clean, loved the gym and cafe!

Reviewed on 10 Oct, 2026

Where to stay in Englewood

Find the best Englewood areas and neighborhoods for the activities you enjoy most. Learn more about Englewood
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 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
A neon sign reading "Blue Chicago on Clark" in an ornate archway.

Magnificent Mile

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

Find hotels in Magnificent Mile
A river with yellow boats, a bridge, and tall buildings.

The Loop

Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.

Find hotels in The Loop
A city street with a train passing overhead, cars, pedestrians, and a red brick building.

River North

Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.

Find hotels in River North
A wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Find hotels in Lincoln Park

Top hotels in Englewood

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
S$177
10 Nov - 11 Nov
includes taxes & fees
Congress Plaza Hotel
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
S$232
25 Oct - 26 Oct
includes taxes & fees
8.8/10 Excellent! (5,513 reviews)
"The staff is so friendly. The location is amazing. I wish the coffee was 24:7 maybe it was just like an off day or so. It was just empty a few times but I sleep in. I loved this place"

Reviewed on 10 Oct, 2026

River Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
S$218
2 Nov - 3 Nov
includes taxes & fees
8/10 Very good! (2,459 reviews)
"We loved the location. The hotel lobby and bar was nice. The breakfast buffet was an average buffet, nothing fancy. Our room was on the small side and the furniture needs some upgrading. The room was clean and we would stay there again. Friendly staff. The person whom booked on Expedia in front of ..."

Reviewed on 10 Oct, 2026

The Chicago Hotel Collection Ambassador Gold Coast
See all 4,644 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.

Frequently asked questions

How much does an Englewood holiday package cost?
Choose from any combination of car rentals, flights and hotels, and you can be holidaying in Englewood from just S$613. And the more you bundle, the more cash you save. Your dream holiday 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 holiday 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 Centre are some interesting ones to put on your to-do list.
How far in advance should I book my Englewood holiday?
While prices change from time to time, we generally recommend booking your holiday 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 holiday is just clicks away.
Can I choose my airline with an Englewood Expedia holiday 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 holiday package?
Certainly, and we're here to help. You may be able to amend or cancel your Englewood holiday 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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

S$31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

S$51
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

S$54
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.