New Orleans, LA (MSY) — $134
Live jazz courtyards in the French Quarter and late-night Creole bistros.
2h 55m · Spirit / Southwest
No Red-Eyes · Fri > 16:00
Weekend Trips for Couples (Under 4 Hours) from Chicago (ORD)
Cheapest Couples & Romantic Getaways deal from Chicago (ORD) this weekend (23/10/2026 – 25/10/2026): $134 roundtrip to New Orleans, LA (MSY) on Spirit / Southwest, departing Friday 18:15, returning Sunday 19:20 (2h 55m). 5 nonstop options verified.
Current Lowest Roundtrip
$134
Typical Weekend Price
$166
Cheapest in Last 8 Weeks
$120
Best Friday Departure Window
Fr 18:15
1. Live Nonstop Weekend Deals from Chicago (ORD)
Weekend Window: 23/10/2026 – 25/10/2026
Updated: 16/10/2026 15:00 · Final price confirmed on click-through
| Route | Carrier | Times (24h) | Duration | Climate / Scope | Roundtrip | Typical / 8w Low | Action |
|---|---|---|---|---|---|---|---|
| Chicago (ORD) → New Orleans, LA (MSY) | Spirit / Southwest | Fr 18:15 · So 19:20 | 2h 55m (Nonstop) | < 4h Flight | $134 | $166 (8w low: $120) | Check Deal |
| Chicago (ORD) → Savannah, GA (SAV) | United / Delta | Fr 17:45 · So 18:50 | 2h 20m (Nonstop) | < 4h Flight | $138 | $171 (8w low: $124) | Check Deal |
| Chicago (ORD) → Charleston, SC (CHS) | Delta / JetBlue | Fr 16:15 · So 17:20 | 2h 15m (Nonstop) | < 4h Flight | $140 | $174 (8w low: $126) | Check Deal |
| Chicago (ORD) → Napa & Sonoma (STS/SFO) (STS) | Alaska / United | Fr 19:45 · So 20:50 | 3h 05m (Nonstop) | < 4h Flight | $163 | $202 (8w low: $149) | Check Deal |
| Chicago (ORD) → Aspen, CO (ASE) | United / American | Fr 16:15 · So 17:20 | 2h 45m (Nonstop) | < 4h Flight | $195 | $242 (8w low: $181) | Check Deal |
2. Curated Destination Mini-Guides & Flight Times
Savannah, GA (SAV) — $138
Spanish-moss squares, boutique riverfront hotels, and walkable wine bars.
2h 20m · United / Delta
Charleston, SC (CHS) — $140
Historic cobblestone district, candlelit Lowcountry dining, and waterfront inns.
2h 15m · Delta / JetBlue
Napa & Sonoma (STS/SFO) (STS) — $163
Vineyard tastings, thermal hot springs, and Michelin-starred farm-to-table dinners.
3h 05m · Alaska / United
Aspen, CO (ASE) — $195
Alpine luxury lodges, mountain gondola views, and fireside aprés lounges.
2h 45m · United / American
3. Frequently Asked Questions (FAQ)
What is the cheapest Couples & Romantic Getaways flight from Chicago this weekend?
For 23/10/2026 – 25/10/2026, the lowest verified nonstop roundtrip from Chicago (ORD) is New Orleans, LA (MSY) at $134 on Spirit / Southwest (departs Friday 18:15, returns Sunday 19:20, flight duration 2h 55m).
How does $134 compare to typical weekend prices from ORD?
The 8-week typical weekend fare for this corridor is $166, with an 8-week floor of $120.
Why does this board exclude layovers and awkward flight times?
Direct routes departing Friday 16:00–21:30, return Sunday >= 12:00, max duration 240 mins, zero layovers. Excludes red-eyes and early Sunday morning flights to ensure a relaxed 48-hour romantic getaway to curated couples destinations.
