South Chicago Holidays from £1,000

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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.
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was £1,282, price is now £1,000 per person
£1,000
per person
14 Aug - 18 Aug
found 7 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
The staff was very friendly and the location was great!

Reviewed on 2 Jul 2026

Nobu Hotel Chicago

Nobu Hotel Chicago

5 out of 5
Downtown Chicago
Price was £1,670, price is now £1,295 per person
£1,295
per person
14 Aug - 18 Aug
found 7 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (873 reviews)
The staff was friendly and helpful. They let us check in early, and I got an upgraded room. Very nice property, I would stay here again.

Reviewed on 2 Jul 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was £1,629, price is now £1,268 per person
£1,268
per person
4 Sept - 8 Sept
found 2 days ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
Very close to shopping, eating, and interstate. Great location. We walked to most of what we wanted to do.

Reviewed on 2 Jul 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was £2,143, price is now £1,670 per person
£1,670
per person
22 Aug - 29 Aug
found 2 hours ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,013 reviews)
This location is ideal for families. The amenities provided are exceptional, scoring a perfect ten out of ten. It offers ample space for a family, including two bathrooms, which was greatly appreciated by my children. The property is well-equipped to ensure a comfortable stay. My only reservation pertains to its distance from Michigan Avenue and the Riverwalk, necessitating a vehicle to access these popular destinations. Otherwise, the experience was flawless.

Reviewed on 2 Jul 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £1,885, price is now £1,475 per person
£1,475
per person
14 Aug - 18 Aug
found 7 hours ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
Great service

Reviewed on 30 Jun 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

5 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

Top hotels in South Chicago

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 £109 per night from 6 Jul to 7 Jul
£109
6 Jul - 7 Jul
includes taxes & fees
8/10 Very good! (10,139 reviews)
"Very cool old hotel in a great location. Well-restored and comfortable. Bell captains were very helpful with suggestions for local attractions and cabs."

Reviewed on 2 Jul 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is £162 per night from 5 Jul to 6 Jul
£162
5 Jul - 6 Jul
includes taxes & fees
9.2/10 Wonderful! (1,830 reviews)
"The staff was very friendly and the location was great!"

Reviewed on 2 Jul 2026

Omni Chicago Hotel
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 £178 per night from 5 Jul to 6 Jul
£178
5 Jul - 6 Jul
includes taxes & fees
9/10 Wonderful! (4,480 reviews)
"Excellent location and beautiful hotel"

Reviewed on 2 Jul 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,195 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

Frequently asked questions

How much does a South Chicago travel package cost?
Explore the best of South Chicago from just £1,000. 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
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.