Business class flights from Chicago (MDW) to Singapore (SIN) start from $2,930 round-trip — up to 40% below published airline prices. The ~17 hours journey covers 9,368 miles, with 3 airlines offering lie-flat seats on this route. Best time to book: 3–6 months in advance for best fares.
MDW → SIN
Chicago to Singapore Business Class
From$2,930
Route Overview
Starting From
$2,930 round-trip
Flight Duration
~17 hours
Distance
9,368 miles
Airlines
3 carriers
Best Value
Jan, Feb, Mar
Savings
Up to 60% off retail
Route Intelligence
Business Class from Chicago to Singapore
Singapore earns its reputation as Asia's premier business gateway, and that's exactly why so many of our Chicago clients fly there in business class rather than economy. Between meetings in the Marina Bay financial district, client dinners in Chinatown or Tiong Bahru, and Changi Airport's consistent ranking as one of the world's best, Singapore rewards travelers who arrive rested. The city also works well as a launch point for onward trips into Southeast Asia, so a comfortable outbound flight matters even more when you've got a full itinerary waiting on the other side.
Airlines & Cabin Experience
From Chicago Midway, this is genuinely an ultra-long-haul journey — 9,368 miles and roughly 17 hours of total travel time once you factor in the connection. MDW is a secondary airport for this route, so your Chicago to Singapore business class itinerary will typically route through a major hub: Atlanta or Minneapolis on Delta, or Houston or Chicago O'Hare on United, before picking up the long-haul leg to Singapore. This isn't a downside so much as a fact of ultra-long-haul travel from the Midwest — the connection gives you a chance to stretch, grab a shower in a lounge, and reset before the marathon leg.
Pricing & Best Time to Fly
Delta's Delta One Suite is the standout hard product here. Each suite has a closing door, a genuine 1-2-1 configuration so window passengers never climb over anyone, and Tumi amenity kits stocked with real skincare rather than an afterthought. On a 17-hour day, that privacy makes a difference — you can work, sleep, or watch a movie without feeling like you're performing for the aisle. United's Polaris product is close behind: lie-flat pods in the same 1-2-1 layout, access to Polaris lounges at connecting hubs (a real perk if you're routing through Houston or ORD), and Saks Fifth Avenue bedding that's noticeably better than the standard blanket-and-pillow combo most US carriers still use.
Why Book Through BestBusinessClass.com
Our fares on this route run $2,930 to $5,430 round-trip, which is typically 30-60% below what you'd find booking directly with the airlines for the same Delta One Suite or Polaris seats. The spread depends heavily on how far out you book and which season you're targeting. January through March and October through December tend to price better than summer, partly because business travel to Singapore's finance and tech sectors is heavier in spring and fall, which pushes premium demand — and prices — up during those windows. If your dates are flexible, shifting even a week or two can mean a meaningfully different fare.
Travel Tips
For the flight itself, a few practical notes. Westbound to Singapore is the easier direction jet-lag-wise since you're generally flying with the sun rather than against it, but 17 hours total is still 17 hours — pack noise-canceling headphones, request an aisle seat if you plan to walk the cabin, and hydrate more than feels necessary given the cabin altitude on that stretch. Because you're connecting rather than flying nonstop, build in at least 90 minutes at your hub for a lounge visit; Delta Sky Clubs and United Polaris lounges both have solid food options that beat anything you'll get on the plane during the first service. Book your Chicago to Singapore business class seat through us early if you want first pick of Delta One Suites or Polaris pods, since those cabins are small and sell out well ahead of peak months.
Airline Comparison
Southwest Airlines
Business Select
Standard seat with priority
Open seating, no baggage fees
Delta Air Lines
Delta One Suite
Suite with closing door, 1-2-1
Delta One Suite privacy, Tumi amenity kit
Read Full Review →
United Airlines
United Polaris
Lie-flat pod, 1-2-1
Polaris lounge access, Saks Fifth Avenue bedding
Read Full Review →Top Rated
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The Business Class Standard
Lie-Flat Guarantee
We only sell true Business Class. 180° fully flat beds on all long-haul routes, ensuring you arrive rested.
Premium Lounges
Access the world's finest lounges. Enjoy pre-flight dining, showers, and quiet workspaces before you board.
Priority Service
Skip the queues. Your ticket includes fast-track security, priority boarding, and premium baggage handling.
The Business Class Standard
Lie-Flat Guarantee
We only sell true Business Class. 180° fully flat beds on all long-haul routes, ensuring you arrive rested.
Premium Lounges
Access the world's finest lounges. Enjoy pre-flight dining, showers, and quiet workspaces before you board.
Priority Service
Skip the queues. Your ticket includes fast-track security, priority boarding, and premium baggage handling.
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