Southwest Side Holidays from £955

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    Save up to £750 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Top Southwest Side Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,347, price is now £955 per person
£955
per person
2 Oct - 7 Oct
found 23 hours ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
8.2/10 Very good! (2,858 reviews)
Had to ask for the room to be cleaned and for new towels, room was super small but made due. Good for short stays

Reviewed on 2 Aug 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,824, price is now £1,186 per person
£1,186
per person
2 Oct - 7 Oct
found 23 hours ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.4/10 Exceptional! (4,770 reviews)

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £1,774, price is now £1,170 per person
£1,170
per person
2 Oct - 7 Oct
found 23 hours ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.2/10 Wonderful! (540 reviews)
Comes with all the comforts of Home.

Reviewed on 29 Jul 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was £1,672, price is now £1,146 per person
£1,146
per person
2 Oct - 7 Oct
found 23 hours ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9/10 Wonderful! (509 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,212, price is now £1,581 per person
£1,581
per person
2 Oct - 7 Oct
found 23 hours ago
Return direct flight included
Birmingham (BHX) to Chicago (ORD)
9.6/10 Exceptional! (1,945 reviews)

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 colorful mural on a concrete wall with various figures and buildings.

Back of the Yards

2 out of top 10 points of interest in this area

While there might not be top attractions in Back of the Yards, you can explore the larger area and discover places like Bridgeport Art Center and Zhou B Art Center.

Find hotels in Back of the Yards

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 £124 per night from 30 Aug to 31 Aug
£124
30 Aug - 31 Aug
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 £141 per night from 17 Aug to 18 Aug
£141
17 Aug - 18 Aug
includes taxes & fees
8/10 Very good! (1,897 reviews)
"Valet parking was full despite booking months in advance"

Reviewed on 2 Aug 2026

The Chicago Hotel Collection Ambassador Gold Coast
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is £143 per night from 30 Aug to 31 Aug
£143
30 Aug - 31 Aug
includes taxes & fees
8.8/10 Excellent! (2,938 reviews)
"Friendly and accommodating staff.. great location near a walking trail"

Reviewed on 2 Aug 2026

Hyatt Regency O'Hare Chicago
See all 4,905 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.
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All Inclusive Holidays
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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

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

£32
per adult
Skydeck Chicago at Willis Tower
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
See all activities in Southwest Side

Frequently asked questions

How much does a Southwest Side travel package cost?
The cheapest Southwest Side package is £955, 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.