Englewood Holidays from £1,436

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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.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was £2,131, price is now £1,436 per person
£1,436
per person
14 Jun - 21 Jun
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
we didn't have breakfast at the hotel

Reviewed on 11 May 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £2,103, price is now £1,493 per person
£1,493
per person
14 Jun - 21 Jun
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (471 reviews)
The rooms were very clean!

Reviewed on 4 May 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was £2,531, price is now £1,804 per person
£1,804
per person
14 Jun - 21 Jun
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.

Reviewed on 8 May 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was £2,556, price is now £1,845 per person
£1,845
per person
14 Jun - 21 Jun
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (3,692 reviews)
London House Hilton Chicago was fabulous. Great location. Wonderful view nice rooms rooftop bar is amazing, make reservations. For a quieter atmosphere the lounge on the second floor is a great place to hang out.. We’ll definitely stay there again.

Reviewed on 11 May 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £3,010, price is now £2,205 per person
£2,205
per person
14 Jun - 21 Jun
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
I LOVE THIS HOTEL!!!

Reviewed on 13 May 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

Top hotels in Englewood

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
The price is £117 per night from 26 May to 27 May
£117
26 May - 27 May
includes taxes & fees
8/10 Very Good! (10,220 reviews)
The bar being open late is nice and the staff are very helpful.

Reviewed on 12 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £152 per night from 25 May to 26 May
£152
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (4,130 reviews)
Breakfast was good.

Reviewed on 13 May 2026

Hotel Riu Plaza Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
The price is £131 per night from 25 May to 26 May
£131
25 May - 26 May
includes taxes & fees
9/10 Wonderful! (4,285 reviews)
Valet and bellmen were great as always. Polite and helpful. The staff brought up an extra valet for my kids on the pullout couch. Great setup for family with kids! And the restaurant on the corner has the best coffee. We stay here every time we visit, can’t beat location, price and separate space ...

Reviewed on 13 May 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,717 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
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Beach Holidays
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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 £1,436. 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

Wrigley Field

4.5/5(40 reviews)

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

Wrigley Field
Navy Pier

Navy Pier

4/5(127 reviews)

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

Navy Pier
Millennium Park

Millennium Park

4.5/5(147 reviews)

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

£28
per adult
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. Flight-inclusive packages are ATOL protected.