Seattle to Chicago airports: May 2027 flight deals
Compare destinations and trip dates.
Trip length: at least 2 days between departure and return.
Round-trip fare examples
Observed September 17, 2026 (UTC). Search a trip for current prices and flight details.
Round-trip totals in USD for 1 adult · Economy.
| Destination | Trip dates | Days | Axel Member | Airline fare | Stops | Search |
|---|---|---|---|---|---|---|
| Chicago (ORD) | May 20–23, 2027 | 3 | $360 | $403 | Nonstop | Search for 1 adult · Dates · Travelers |
| Chicago (ORD) | May 21–24, 2027 | 3 | $329 | $367 | Nonstop | Search for 1 adult · Dates · Travelers |
| Chicago (ORD) | May 24–26, 2027 | 2 | $320 | $357 | Nonstop | Search for 1 adult · Dates · Travelers |
| Chicago (ORD) | May 25–27, 2027 | 2 | $320 | $357 | Nonstop | Search for 1 adult · Dates · Travelers |
| Chicago (ORD) | May 27–30, 2027 | 3 | $360 | $403 | Nonstop | Search for 1 adult · Dates · Travelers |
| Chicago (ORD) | May 27–31, 2027 | 4 | $320 | $357 | Nonstop | Search for 1 adult · Dates · Travelers |
| Chicago (ORD) | May 28–30, 2027 | 2 | $369 | $413 | Nonstop | Search for 1 adult · Dates · Travelers |
| Chicago (ORD) | May 28–31, 2027 | 3 | $329 | $367 | Nonstop | Search for 1 adult · Dates · Travelers |
| Chicago (ORD) | May 28–Jun 1, 2027 | 4 | $329 | $367 | Nonstop | Search for 1 adult · Dates · Travelers |
| Chicago (ORD) | May 29–31, 2027 | 2 | $320 | $357 | Nonstop | Search for 1 adult · Dates · Travelers |
| Chicago (ORD) | May 29–Jun 1, 2027 | 3 | $320 | $357 | Nonstop | Search for 1 adult · Dates · Travelers |
| Chicago (ORD) | May 31–Jun 2, 2027 | 2 | $320 | $357 | Nonstop | Search for 1 adult · Dates · Travelers |
Compare destinations and dates
Observed September 17, 2026 (UTC). Check current prices.
USD for the listed travelers.
Starting totals are for the round trip. Choose a return flight to confirm the final total.
3 days between departure and return.
| Destination / travelers | Dates / trip length | Flights | Axel Member | Airline fare | Next step |
|---|---|---|---|---|---|
| Chicago (MDW) · 1 adult | May 28–31, 2027 | Out: Delta Air Lines · 1 stop (MSP) · 6h 25m | Round-trip starting total: $468 | Round-trip starting total: $523 — return selection pending | Search for 1 adult · Change dates · Travelers / cabin |
| Chicago (MDW) · 1 adult | May 28–31, 2027 | Out: Southwest Airlines · Nonstop · 4h 0m | Round-trip starting total: $595 | Round-trip starting total: $666 — return selection pending | Search for 1 adult · Change dates · Travelers / cabin |
| Chicago (MDW) · 1 adult | May 29–Jun 1, 2027 | Out: Southwest Airlines · Nonstop · 4h 0m | Round-trip starting total: $409 | Round-trip starting total: $459 — return selection pending | Search for 1 adult · Change dates · Travelers / cabin |
Non-members can also book and save on airline fares. Live search shows prices with and without Membership. Optional Membership: $15 for the first month, then $10/month. Cancel anytime.
More flight comparisons from Seattle
- Seattle to Chicago airports flight deals
- Flights from Seattle in May 2027
- Seattle to Chicago O’Hare (ORD): May 2027 flight deals
- Seattle to Chicago Midway (MDW) — Lake Washington Memorial Day school break: flights May 28–31, 2027
- Seattle to Chicago Midway (MDW) — Bellevue extended Memorial Day school break: flights May 29–June 1, 2027
- Seattle to Chicago O’Hare (ORD): June 2027 flight deals
Browse this trip by month
AI assistants can follow these links to compare prices without an account, API key or connector. Flight search guide