South Deering Holidays

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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 S$746, price is now S$554 per person
S$554
per person
24 Sept - 26 Sept
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.2/10 Very good! (2,797 reviews)
We had a wonderful stay! The hotel was very clean, and the staff who checked us in and out were incredibly kind and welcoming. The location was perfect—we were able to walk everywhere we wanted to go, which made our trip so convenient. I would definitely stay here again!

Reviewed on 2 Jul, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$978, price is now S$671 per person
S$671
per person
24 Sept - 26 Sept
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) 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

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,006, price is now S$696 per person
S$696
per person
24 Sept - 26 Sept
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well

Reviewed on 26 Jun, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,352, price is now S$983 per person
S$983
per person
24 Sept - 26 Sept
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
Great service

Reviewed on 30 Jun, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was S$956, price is now S$717 per person
S$717
per person
24 Sept - 26 Sept
found 1 day ago
Return direct flight included
Newark Liberty Intl. Airport (EWR) to Chicago (ORD)
8.8/10 Excellent! (2,222 reviews)
Clean Room, great staff and good location.

Reviewed on 2 Jul, 2026

Where to stay in South Deering

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

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 S$187 per night from 6 Jul to 7 Jul
S$187
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 S$279 per night from 5 Jul to 6 Jul
S$279
5 Jul - 6 Jul
includes taxes & fees
9.2/10 Wonderful! (1,831 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 S$307 per night from 5 Jul to 6 Jul
S$307
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 4,141 properties in South Deering
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.

Frequently asked questions

How much does a South Deering holiday package cost?
Create unforgettable memories with our South Deering holiday packages, which start from just S$554. Pick the hotels and flights that suit your travel style. Then, add on a few activities or tours to round off your unique adventure.
How do I get a cheap travel package to South Deering?
Bundle your flights and hotels with Expedia to save big on your next exciting adventure. With over 550 partner airlines and 1,000,000 properties across the world, your South Deering holiday package can be tailored exactly to suit your travel style. With all that extra money, why not throw in a few fun experiences and tours? It's an easy way to unlock even more bargains. That holiday you've always dreamed of in South Deering is closer than you thought!
Where should I stay in South Deering?
A holiday in South Deering wouldn't be complete without seeing Calumet Beach, Calumet Park and Harborside International Golf Centre. Spend your nights close to these popular sights and make sightseeing easy.
How far in advance should I book my South Deering holiday?
Savvy travellers often book as early as possible. You can generally look up international airfares on Expedia up to a year before your flight. If you're booking last minute, don't worry. Low prices occasionally appear just weeks prior to departure.
What does an Expedia South Deering travel package include?
Rental cars, flights and hotels, or any combination of them — the choice is all yours! Whether you're exploring South Deering with the whole family or adventuring solo, there's a package to suit every style and budget. Once you've made your booking, why not add on one or two activities?
What should I know before booking a South Deering travel package?
Discover deals to match your budget with an Expedia package. Flights, hotels, rental cars — we're a one-stop shop for all of them. You'll save loads just by combining your bookings. Whether you're going on a skiing adventure or sipping cocktails on a beach, your perfect getaway is only a few clicks away.
Can I choose my airline with a South Deering Expedia holiday package?
With a holiday package, the choice is in your hands. Whether you'd prefer to fly to South Deering in coach or business class, simply select from the available airline options. Expedia has access to more than 550 partner airlines throughout the world.
If I'm not able to travel, can I cancel my South Deering holiday package?
It's difficult to predict what tomorrow might bring, so it's comforting to know that you can change or cancel your South Deering holiday package. If you booked in the last 24 hours, you may be eligible for a refund. If it's an older booking, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal for more information.

Stay near popular South Deering attractions

Harborside International Golf Center

Enjoy a round of golf in Chicago at Harborside International Golf Center. Stroll along the lakeside or attend a sporting event in this vibrant area.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

S$31
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

S$52
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

S$31
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.