$341 Cheap flight deals from Chicago (CHI) to South West Division (SG-05)

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This Weekend's Flight Deals from Chicago to South West Division

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Sat, Jan 31 - Fri, Feb 6
ORD
O'Hare Intl.
SIN
Changi
$914 Roundtrip, found 6 days ago
$914
Roundtrip
found 6 days ago
Select Turkish Airlines flight, departing Sat, Jan 31 from O'Hare Intl. to Changi, returning Fri, Feb 6, priced at $914 found 6 days ago

Airfares from $341 One Way, $822 Round Trip from Chicago to South West Division

Prices starting at $822 for return flights and $341 for one-way flights to South West Division were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, Feb 16 - Sun, Apr 12
ORD
Chicago
SIN
Singapore
$822 Roundtrip, found 2 hours ago
$822
Roundtrip
found 2 hours ago
Select Air India flight, departing Mon, Feb 16 from Chicago to Singapore, returning Sun, Apr 12, priced at $822 found 2 hours ago
Mon, Oct 5 - Tue, Oct 20
ORD
Chicago
SIN
Singapore
$862 Roundtrip, found 9 hours ago
$862
Roundtrip
found 9 hours ago
Select Turkish Airlines flight, departing Mon, Oct 5 from Chicago to Singapore, returning Tue, Oct 20, priced at $862 found 9 hours ago
Mon, Feb 16 - Tue, Apr 14
ORD
Chicago
SIN
Singapore
$881 Roundtrip, found 5 days ago
$881
Roundtrip
found 5 days ago
Select United flight, departing Mon, Feb 16 from Chicago to Singapore, returning Tue, Apr 14, priced at $881 found 5 days ago
Thu, Nov 19 - Thu, Nov 26
ORD
Chicago
SIN
Singapore
$884 Roundtrip, found 2 days ago
$884
Roundtrip
found 2 days ago
Select Korean Air flight, departing Thu, Nov 19 from Chicago to Singapore, returning Thu, Nov 26, priced at $884 found 2 days ago
Mon, Feb 16 - Tue, Apr 14
ORD
Chicago
SIN
Singapore
$894 Roundtrip, found 5 days ago
$894
Roundtrip
found 5 days ago
Select Delta flight, departing Mon, Feb 16 from Chicago to Singapore, returning Tue, Apr 14, priced at $894 found 5 days ago

South West Division economy flight packages

Price found within the past 48 hours. Click for updated prices.
Creekside Inn
2.5-star property

Creekside Inn

8/10 Very Good! (1,004 reviews)

Mar 5 - Mar 8

3 night stay

Chicago (CHI) to Miami (MIA)

Spirit Airlines • Roundtrip • Coach
Price was $976, price is now $478 per person
$478
per person
found 1 day ago
I only stayed one night but overall, Creekside was better than I was expecting. For an old keys motel type inn, it was very clean and well kept.

Reviewed on Aug 2, 2025

Royal Sun Palm Springs
4.0-star property

Royal Sun Palm Springs

8.4/10 Very Good! (236 reviews)

Feb 26 - Mar 2

4 night stay

Chicago (CHI) to Los Angeles (LAX)

American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,195, price is now $586 per person
$586
per person
found 1 day ago
Cavalier Hotel South Beach
3.5-star property

Cavalier Hotel South Beach

8.4/10 Very Good! (1,001 reviews)

Feb 28 - Mar 5

5 night stay

Chicago (CHI) to Miami (MIA)

Spirit Airlines • Roundtrip • Coach
Price was $1,271, price is now $629 per person
$629
per person
found 1 day ago
Staff was great, elevator is tired, but I loved the proximity to everything

Reviewed on Jan 3, 2026

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South West Division first class flight packages

Price found within the past 48 hours. Click for updated prices.
Hotel Valley Ho
4.5-star property

Hotel Valley Ho

9.6/10 Exceptional! (2,097 reviews)

Mar 18 - Mar 25

7 night stay

Chicago (CHI) to Phoenix (PHX)

American Airlines • Non-stop • FirstClass

Phoenix (PHX) to Chicago (CHI)

United • Non-stop • FirstClass
Price was $3,002, price is now $2,092 per person
$2,092
per person
found 1 day ago
Great place in old town

Reviewed on Jan 5, 2026

Isla Bella Beach Resort & Spa
5.0-star property

Isla Bella Beach Resort & Spa

9.2/10 Wonderful! (1,055 reviews)

Mar 11 - Mar 18

7 night stay

Chicago (ORD) to Miami (MIA)

American Airlines • Roundtrip • FirstClass
Save 100% on your flight
Price was $7,097, price is now $4,871 per person
$4,871
per person
found 2 hours ago
Mattress encased in plastic. First place I’ve seen that. Really helped my dust mite allergy. Fantastic place in all aspects. We will be back as now one of our favorite places to stay.

Reviewed on Dec 18, 2025

The Avalon Club
4.0-star property

The Avalon Club

9.4/10 Exceptional! (481 reviews)

Mar 15 - Mar 21

6 night stay

Chicago (ORD) to Tampa (TPA)

United • Roundtrip • FirstClass
Save 100% on your flight
Price was $5,067, price is now $3,611 per person
$3,611
per person
found 24 hours ago
You can walk to different restaurants. The only bad thing is that the bed in the master bedroom was not in good condition and the metal base was broken. I had to move to another room within the same unit.

Reviewed on Aug 17, 2025

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More About Flying To South West Division from Chicago

Route Information for Flights from Chicago to South West Division

Origin Airport IATA Code
CHI
Destination Airport IATA Code
SG-05
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Chicago to South West Division

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.