Englewood Holidays from £1,234

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

Downtown Chicago
£1,234
per person
19 Sept - 26 Sept
found 13 hours ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
8.2/10 Very good! (2,879 reviews)
We visited gor an extended weekend birthday celebration. The hotel was centrally located about 15 minutes walking away from the Magnificent Mile. Restuarants are near by and Walgreens. The staff was very nice and accommodating. A special shout-out to Aldo for his professionalism and helpfulness.

Reviewed on 11 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
Save 100% on your flight
£1,542
per person
19 Sept - 26 Sept
found 13 hours ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
£2,004
per person
14 Oct - 20 Oct
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The

Reviewed on 10 Aug 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
Save 100% on your flight
£1,471
per person
19 Sept - 26 Sept
found 13 hours ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
I’m okay on them

Reviewed on 11 Aug 2026

Level Chicago - River North

Level Chicago - River North

Downtown Chicago
Save 100% on your flight
£1,457
per person
19 Sept - 26 Sept
found 13 hours ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.2/10 Wonderful! (1,043 reviews)

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.

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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.

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

Magnificent Mile

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

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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.

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A nighttime cityscape with fireworks over a body of water, a Ferris wheel, and illuminated buildings.

Theatre District

While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).

Find hotels in Theatre District

Top hotels in Englewood

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£94
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,288 reviews)
"Lower price$"

Reviewed on 11 Aug 2026

Congress Plaza 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
£126
30 Aug - 31 Aug
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
£200
11 Sept - 12 Sept
includes taxes & fees
Hilton Chicago O'Hare Airport
See all 4,547 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
Family Friendly Holidays
Family Friendly Holidays
Golf Holidays
Golf Holidays
Luxury Holidays
Luxury Holidays
gay friendly holidays
LGBTQ+ Holidays
LGBTQ+ Holidays
Romantic Holidays
Romantic Holidays
Ski Holidays
Ski Holidays
Pet Friendly Holidays
Pet Friendly Holidays
Holiday in Month
Where to go when
Where to go when

Frequently asked questions

How much does an Englewood travel package cost?
Get your credit card ready, because a trip to Englewood starts from only £1,234. 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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

£35
per adult
88% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.