South Chicago Holidays from £1,397

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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 Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,849, price is now £1,397 per person
£1,397
per person
31 Jul - 5 Aug
found 12 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
8.2/10 Very Good! (2,683 reviews)
It was very close to restuarants, easy to find and very accessible. All staff were really helpful.

Reviewed on 16 May 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,895, price is now £1,789 per person
£1,789
per person
31 Jul - 5 Aug
found 12 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9/10 Wonderful! (3,319 reviews)
2 blocks off Michigan ave, 1 block to the river, and great views of Lake Michigan. Staff was very helpful and kind.

Reviewed on 15 May 2026

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 £2,406, price is now £1,723 per person
£1,723
per person
31 Jul - 5 Aug
found 12 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (2,505 reviews)
Amazing hotel. I would stay again.

Reviewed on 15 May 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was £2,347, price is now £1,690 per person
£1,690
per person
31 Jul - 5 Aug
found 12 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (3,692 reviews)
I had a great stay and would book again.

Reviewed on 15 May 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was £1,990, price is now £1,543 per person
£1,543
per person
31 Jul - 5 Aug
found 12 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
8.8/10 Excellent! (2,144 reviews)
Staff was very good, attentive. The property itself is in a great location, but the room showed some wear and tear - exposed drywall screws holding on bathroom door trim with some paint slapped on it, smelly sink, water damage and peeling paint on inside window sill, visually boring interior that looks like it's from the 1990's

Reviewed on 12 May 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
Downtown Chicago

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 £119 per night from 26 May to 27 May
£119
26 May - 27 May
includes taxes & fees
8/10 Very Good! (10,132 reviews)
Great location of the hotel on Michigan Ave. Close to multiple “L” stations. Felt walking around the hotel. Got back from a baseball game around 10pm on a weekday and had no issues. Room was clean. Cool historic hotel

Reviewed on 16 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £154 per night from 25 May to 26 May
£154
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (4,155 reviews)
Roof top bar

Reviewed on 15 May 2026

Hotel Riu Plaza Chicago
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is £128 per night from 25 May to 26 May
£128
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (5,182 reviews)
The staff was excellent especially Ronnie and Pedro they both went beyond the call of duty to help and assist me and my group also the hotel not far from the Riverwalk

Reviewed on 16 May 2026

River Hotel
See all 4,395 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
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Family Friendly Holidays

Frequently asked questions

How much does a South Chicago travel package cost?
Explore the best of South Chicago from just £1,397. 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.

Popular places to visit

Wrigley Field

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Millennium Park

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

£29
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
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.