Southwest Side Holidays from £793

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Top Southwest Side Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was £1,099, price is now £793 per person
£793
per person
14 Jan - 21 Jan
found 9 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (1,009 reviews)

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 £1,318, price is now £977 per person
£977
per person
21 Jan - 26 Jan
found 9 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,077, price is now £820 per person
£820
per person
2 Dec - 9 Dec
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
8.4/10 Very good! (3,148 reviews)

Hotel Saint Clair- Magnificent Mile

Hotel Saint Clair- Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,082, price is now £829 per person
£829
per person
14 Jan - 21 Jan
found 9 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (2,334 reviews)
Everything was really nice. But we didn't have room service. And the sink had been clogged since the day we arrived.

Reviewed on 1 Nov 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was £1,113, price is now £854 per person
£854
per person
14 Jan - 21 Jan
found 9 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,881 reviews)
First time staying there. The room was nice, clean and the bed was comfortable. The hotel is so conveniently located from the riverwalk, boat tours and shopping.

Reviewed on 1 Nov 2026

Where to stay in Southwest Side

Find the best Southwest Side areas and neighborhoods for the activities you enjoy most. Learn more about Southwest Side
A waterfront promenade with a distinctive green-domed building, a city skyline in the background, and a clear blue sky.

Englewood

1 out of top 10 points of interest in this area

While you're strolling through Englewood, you may want to check out the beaches and restaurants. If you want to see more of the area, hop on the metro at Halsted Station or 63rd Station.

Find hotels in Englewood

Southwest Side Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)

Top hotels in Southwest Side

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 £103 per night from 10 Nov to 11 Nov
£103
10 Nov - 11 Nov
includes taxes & fees
Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is £130 per night from 22 Nov to 23 Nov
£130
22 Nov - 23 Nov
includes taxes & fees
8/10 Very good! (2,639 reviews)
"My room phone did not work and think it would be great to see a vending machine with needed items like Coke and snacks. Also think the staff could be dressed in a great uniform to represent the history of hotel in a modern way. I would be glad to have a call from hotel to discuss conversation or ..."

Reviewed on 2 Nov 2026

The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is £99 per night from 26 Nov to 27 Nov
£99
26 Nov - 27 Nov
includes taxes & fees
River Hotel
See all 5,067 properties in Southwest Side
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

Stay near popular Southwest Side attractions

Marquette Park

9.4/10 (3 reviews)
After visiting Marquette Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.
See properties

What to do in Southwest Side

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

£32
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
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 Southwest Side

Frequently asked questions

How much does a Southwest Side travel package cost?
The cheapest Southwest Side package is £793, so your dream escape can become a reality — without breaking the bank. Bundle flights, hotels and car rentals to build a package that's perfect for you.
If I'm not able to travel, can I cancel my Southwest Side travel package?
If your holiday plans in Southwest Side have been upended, it's comforting to know that it is possible to amend or cancel your booking. If you booked less than 24 hours ago, you may be able to get a refund. If your booking was made more than 24 hours ago, your hotel, airline or car rental company may impose a fee. For more information, check our Customer Service Portal.
How do I get a cheap travel package to Southwest Side?
Bundle your bookings with Expedia to save on your next adventure. With over 550 airlines and 1,000,000 hotels globally, your Southwest Side travel package can be customized exactly to suit your budget. With all that extra cash, why not add one or more interesting experiences and tours? It's an easy way to unlock even more discounts. That dream holiday to Southwest Side is much closer than you thought!
Does Expedia offer Book Now, Pay Later Southwest Side holidays?
Your bank balance shouldn't prevent you from escaping on holiday, so Expedia has devised 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 eating away at your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your trip. Check out these flexible payment options:

  • Pay monthly holidays: Make your holiday dreams a reality sooner with Klarna's convenient monthly instalment plans. If paying a little each month works for you, pick this option at checkout.
  • Pay in instalments holidays: If you'd prefer to pay for your escape in multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than all of it upfront) makes it easier to click that "book now" button, go for a low deposit holiday payment plan with Klarna.

How far in advance should I book my Southwest Side holiday?
To bag discount prices, book early. Air carriers usually release flights, along with some of the lowest fares, nearly 12 months ahead of time. Hotels, car rental and experiences should also be booked early to avoid disappointment. If you're in need of a last-minute getaway to Southwest Side, there are always plenty of great deals on Expedia. Check them out now!
What does an Expedia Southwest Side travel package include?
Much of that is up to you. You can choose from a variety of Southwest Side packages, such as a hotel, flight and rental car. You can also book a flight with a hotel, or a rental car and a flight. Once you've made your booking, you can add on the fun stuff like tours and activities. Whatever your Southwest Side break looks like, you're sure to save!
What should I know before booking a Southwest Side travel package?
Bundling your bookings into a Southwest Side travel package is the most convenient way to organise your trip. Not only that, you'll save big just for combining your hotels, flights and car rentals. Once you've booked, why not add on a tour or an activity?
Can I choose my airline with a Southwest Side Expedia travel package?
Most definitely. We have access to over 550 partner airlines throughout the world, so you can customize your Southwest Side trip according to your style and budget.

Explore a world of travel with Expedia

* 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.