Englewood Holidays from £933

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Your Englewood Holiday

Make travel planning stress-free by snapping up a holiday package to Englewood. Let us look after the minutiae, so you can concentrate on soaking up everything this neighbourhood can offer. Hoping to sightsee during your trip to Englewood? Be sure to stop by nearby attractions such as University of Chicago, Robie House and 4944 S Woodlawn Ave. Don't just wish for it — do it! Book your perfect Englewood holiday with Expedia and travel your way.

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

Arlo Chicago

4 out of 5
Downtown Chicago
per person
17 Sept - 22 Sept
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,831 reviews)
A great boutique property in the heart of old town Chicago! Close to parks, transportation, and many dining and entertainment options.

Reviewed on 5 Aug 2025

The Wade

The Wade

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
13 Oct - 20 Oct
found 3 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
8.2/10 Very Good! (1,156 reviews)
This was my second time staying here. I love the location! The front desk and cleaning staff were amazing! My only complaint is not having free wifi but everything else is wonderful.

Reviewed on 5 Aug 2025

Radisson Blu Aqua Hotel Chicago

Radisson Blu Aqua Hotel Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
13 Oct - 20 Oct
found 3 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
8.4/10 Very Good! (1,586 reviews)
The property was nice but overcharged everything not worth the value.

Reviewed on 8 Aug 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
13 Oct - 20 Oct
found 3 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
8.2/10 Very Good! (1,991 reviews)
Hotel location is close to Michigan ave and very convenient to local dining and attractions, unfortunately city is becoming unsafe and dirty, is not what used to be years back.

Reviewed on 7 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
7 Sept - 11 Sept
found 5 hours ago
Return direct flight included
Glasgow (GLA) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Everything is nice specially stuff hosptality

Reviewed on 8 Aug 2025

Where to stay in Englewood

Find the best Englewood areas and neighborhoods for the activities you enjoy most. Learn more about Englewood
Downtown Chicago featuring a city

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

Top hotels in Englewood

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 £117 per night from 21 Aug to 22 Aug
£117
21 Aug - 22 Aug
includes taxes & fees
7.8/10 Good! (8,921 reviews)
"Took water awhile to get hot for shower, and parking is ridiculously expensive. Other than that enjoyed staying at hotel"

Reviewed on 8 Aug 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £170 per night from 22 Aug to 23 Aug
£170
22 Aug - 23 Aug
includes taxes & fees
8.2/10 Very Good! (1,831 reviews)
"Great!"

Reviewed on 5 Aug 2025

Palmer House a Hilton Hotel
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is £128 per night from 24 Aug to 25 Aug
£128
24 Aug - 25 Aug
includes taxes & fees
8.8/10 Excellent! (1,345 reviews)
"My wife and daughter loved there was a Starbucks a short walk down the street, maybe 5 minutes, this was their morning routine. The restaurant was good, prices were in line with other spots in the area, however, I did not like being told the restaurant closes at 9:30, even though hours say 10. Not ..."

Reviewed on 5 Aug 2025

Crowne Plaza Chicago West Loop by IHG
See all 4,640 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does an Englewood travel package cost?
Get your credit card ready, because a trip to Englewood starts from only £933. When you bundle your flights, hotels and more into a travel package, you'll score the best prices.
If I'm not able to travel, can I cancel my Englewood travel package?
Don't worry if you're rethinking your Englewood travel package — it's possible to cancel or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur a fee from your hotel, airline or car rental company. We get that life can throw the occasional spanner in the works, so look up our Customer Service Portal if that happens. When you're ready to make changes, we'll take care of it.
How do I get a cheap travel package to Englewood?
Crafting your own Englewood travel package with Expedia is one of the easiest ways to save. We offer more than 550 airlines and 1,000,000 hotels all over the world. With such an amazing range to choose from, you'll have no issues putting together your perfect getaway.
Does Expedia offer Book Now, Pay Later Englewood holidays?
Your bank balance shouldn't get in the way of going on holiday, so Expedia has worked out a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book a fantastic getaway without making a dent in your savings. Klarna offers flexible payment options at checkout that take the stress out of budgeting for your break. Consider one of these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month is what works best for you, Klarna offers just that! Paying in convenient monthly instalments will make your holiday dreams come true.
  • Pay in instalments holidays: Like the idea of paying off your holiday in multiple transactions? Then select this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the full total upfront) makes it easier to hit that "book now" button, choose a low deposit holiday payment plan with Klarna.

Where should I stay in Englewood?
A journey to Englewood isn't complete until you've seen Millennium Park and Wrigley Field. Book a hotel nearby and easily access these famous attractions.
What are the top hotels in Englewood?
Get your holiday off to a good start by reserving a room at Hyatt Regency Chicago. It's one of most sought-after hotels in Englewood. Another cosy option is The Godfrey Hotel Chicago.
How far in advance should I book my Englewood holiday?
Earlier is always better. Air carriers usually release flights nearly 12 months ahead of departure, and this is a fantastic opportunity to land some of the cheapest prices. Boss just told you to use up all your holiday days next month? No need to worry. Expedia are never short of fantastic bargains to whisk you away on the getaway of your dreams, at a price you can afford.
What does an Expedia Englewood travel package include?
Expedia has all you need to organise your Englewood escape, but how your package is structured is your choice. Select from a combination of hotels, flights and rental cars. In search of some activities or tours to keep you busy? Once you've made your booking, you can add them on too. Whatever your budget, there's a package deal to suit your needs.
What should I know before booking an Englewood travel package?
A package can be easier on the bank balance than individually booking all you need for your trip. For example, combine your hotels, flights and rental cars and land a great deal. Whatever your holiday plans, you'll find a package that fits your budget.
Can I choose my airline with an Englewood Expedia travel package?
With a travel package, you're in charge. Whether you're eager to fly to Englewood in first class or coach, simply pick from the available airline options. Expedia has access to over 550 partner airlines around the world.

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North which includes street scenes, signage and night scenes

Michigan Avenue

You can find the perfect gifts to bring home 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
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

Things to do

River tour boat in Chicago

Architecture River Tour

£31
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
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. Flight-inclusive packages are ATOL protected.