South Chicago Holidays from £818

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Your South Chicago Holiday

Booking a South Chicago holiday package is a wonderful way to become acquainted with this unique neighbourhood. From its must-visit places to its little-known delights, you won't be short of new adventures. Kick start your trip to South Chicago by visiting nearby attractions such as Jackson Park, Calumet Park and Calumet Beach. Stop daydreaming and start doing. When you're ready to book your dream holiday to South Chicago, Expedia will help get you there.

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
£818
per person
26 Dec - 31 Dec
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
£1,305
per person
26 Dec - 31 Dec
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
£834
per person
26 Dec - 31 Dec
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
£1,104
per person
1 Dec - 4 Dec
found 20 hours ago
Return direct flight included
Newcastle (NCL) to Chicago (ORD)
9/10 Wonderful! (3,518 reviews)
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago
£863
per person
26 Dec - 31 Dec
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (3,877 reviews)
I loved this hotel from top to Bottom

Reviewed on 3 Oct 2026

Where to stay in South Chicago

Find the best South Chicago areas and neighborhoods for the activities you enjoy most. Learn more about South Chicago
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.

Find hotels in Downtown Chicago
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.

Find hotels in Magnificent Mile
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.

Find hotels in The Loop
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 wooden pavilion with a view of a city skyline and a body of water.

Lincoln Park

Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.

Find hotels in Lincoln Park

Top hotels in South Chicago

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£105
3 Nov - 4 Nov
includes taxes & fees
8/10 Very good! (10,162 reviews)
"Room was clean, staff were friendly and the bar was relaxing."

Reviewed on 4 Oct 2026

Congress Plaza Hotel
River Hotel

River Hotel

75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
£142
2 Nov - 3 Nov
includes taxes & fees
River 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
£128
1 Nov - 2 Nov
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
See all 4,333 properties in South Chicago
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
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 a South Chicago travel package cost?
Explore the best of South Chicago from just £818. Choose from a great selection of flights, rental cars and hotels to suit your budget. Pick up even better deals when you add a couple of experiences or tours to your travel package.
If I'm not able to travel, can I cancel my South Chicago travel package?
Your situation can change unexpectedly, so yes. You may be able to cancel or alter your South Chicago travel package at no cost within 24 hours of booking. For bookings older than that, you can still make the necessary changes, but your car rental company, hotel or airline may impose a charge. Want more information? Look up our Customer Service Portal. We're here to help make sure your getaway goes off without a hitch.
How do I get a cheap travel package to South Chicago?
Booking a flight and hotel together with Expedia won't just save you time — it'll save you cash too. A South Chicago travel package makes it simple to create your ideal trip. With more than 550 airlines worldwide to choose from, finding flights that suit your schedule won't be difficult. In addition to that, we have over 1,000,000 properties globally to select from. Talk about choice! No matter who you are, Expedia puts more of the world within your reach.
Does Expedia offer Book Now, Pay Later South Chicago holidays?
Your bank balance shouldn't prevent you from going on holiday, so Expedia has come up with a solution to help. Now that we've partnered with online lender Klarna, it's easier than ever to book an incredible getaway without making a dent in your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your escape. Check out these flexible payment options:
  • Pay monthly holidays: If paying small amounts each month is what works best for you, Klarna can help. Paying in convenient monthly instalments will make your holiday dreams come true.
  • Pay in instalments holidays: If you'd like to pay off 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: When you want to jump on an amazing deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you get what you want.
Where should I stay in South Chicago?
Take the hassle out of sightseeing by staying just around the corner from South Chicago's biggest attractions. Millennium Park and Wrigley Field are two visitor favourites.
What are the top hotels in South Chicago?
Hyatt Regency Chicago and The Godfrey Hotel Chicago are among the most sought-after hotels in South Chicago. Why not have a look at the facilities and amenities at each and then decide?
How far in advance should I book my South Chicago holiday?
Travellers are usually able to browse international airfares on Expedia up to 12 months prior to departure. Booking late? With a stroke of luck, it's still possible to score a cheap ticket just weeks before your flight.
What does an Expedia South Chicago travel package include?
Rental cars, flights and hotels, or any combination of them — it's your choice. Whether you're headed to South Chicago on a family road trip or travelling with your friends, there's a package to suit every budget and style. Once you've made your booking, why not add on a few activities?
What should I know before booking a South Chicago travel package?
Tailor deals that fit your budget with an Expedia package. Hotels, airfares, rental cars — we've got all of them. You'll save big bucks just by bundling your bookings. Whether you're going on a snow and ski adventure or sunning yourself on a warm beach, your dream getaway is only clicks away.
Can I choose my airline with a South Chicago Expedia travel package?
Expedia offers access to more than 550 airline partners globally, so you certainly can. Simply choose your favourite carrier and put together the perfect South Chicago holiday.

Stay near popular South Chicago attractions

Mahalia Jackson Residence

You can find out about the history of Chicago with a stop at Mahalia Jackson Residence. Experience the area's entertainment choices and live music.
See properties

Things to do

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
88% 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 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.