Southwest Side Holidays from £1,297

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Top Southwest Side Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
9 Oct - 15 Oct
found 20 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,053 reviews)
The building and rooms were beautiful, and clean. You cannot beat the views of the lake and the night skyline. We had a problem with the elevator keycard access not working but security helped us out. My biggest gripe is not having more options to order for room service from ther hotel restaurant. We didnt want to pay $70 for two burgers, and we didnt want to go out after a long day of traveling. We did door dash pizza, and everything was fine. Other than that, it was a very nice stay.

Reviewed on 28 Jul 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
9 Oct - 15 Oct
found 20 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (324 reviews)
I liked the hotel room's kitchen and it is very nice, however VERY small. The pool/amenities are also very nice. One major challenge was there was a last minute change to the location of our reservation from old town to fulton market. They did communicate the change and provided a discount, however, this occurred the day before our trip. The check-in process was also very disorganized and confusing. Information easily accessible in the reservation was not used, requiring extra check-in time. They told us a crib was available, and later found only a pack and play. I requested bedding for the pull out 4 times before someone brought them. Overall, management needs to improve their operations.

Reviewed on 21 Jul 2025

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
9 Oct - 15 Oct
found 20 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
8.2/10 Very Good! (1,842 reviews)
The room ended up being quieter than I would have expected since it’s right next to one elevator bank and across the hall from the other. I was told upon check in that they would move me to another room down the hall. When we came back at 4 I was told that there was no note for that request and that there were no more King rooms. Overall the room was fine, nothing special.

Reviewed on 28 Jul 2025

Staypineapple, An Iconic Hotel, The Loop

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
9 Oct - 15 Oct
found 20 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,011 reviews)
It was a perfect overnight stay in Chicago. Easy accessibility, clean & helpful staff.

Reviewed on 28 Jul 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
9 Oct - 15 Oct
found 20 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on 22 Jul 2025

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
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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 £117 per night from 21 Aug to 22 Aug
£117
21 Aug - 22 Aug
includes taxes & fees
7.8/10 Good! (8,992 reviews)
"Hotel was beautiful"

Reviewed on 27 Jul 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is £243 per night from 10 Aug to 11 Aug
£243
10 Aug - 11 Aug
includes taxes & fees
9/10 Wonderful! (2,129 reviews)
Overall a great family hotel
"Great time in Chicago and the hotel made it phenomenal! It’s in a very central location and allows access to all the major tourist attractions within walking distance. We really enjoyed Saturday movie night at the pool!"

Reviewed on 28 Jul 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £126 per night from 17 Aug to 18 Aug
£126
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (2,548 reviews)
"Great area, clean hotel but, parking is expensive. There was no pool."

Reviewed on 27 Jul 2025

Hilton Chicago/Magnificent Mile Suites
See all 5,012 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
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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

What to do in Southwest Side

River tour boat in Chicago

Architecture River Tour

£36
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£33
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Southwest Side

Frequently asked questions

How much does a Southwest Side travel package cost?
The cheapest Southwest Side package is £1,297, 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.

* 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.