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San Antonio → Chicago

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SAT → MDW1 adulteconomy

24 flight options · 2 airlines

Round-trip flights

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
6:25 amSAT
2h 30m
Nonstop
8:55 amMDW
Southwest Airlines
9:30 pmMDW
3h
Nonstop
12:30 am+1SAT

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Delta Air Lines
5:25 amSAT
7h 36m
DTW · 3h 16m
1:01 pmMDW
Delta Air Lines
9:30 amMDW
6h 33m
DTW · 1h 57m
4:03 pmSAT

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
2:50 pmSAT
2h 35m
Nonstop
5:25 pmMDW
Southwest Airlines
8:50 pmMDW
2h 55m
Nonstop
11:45 pmSAT

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
2:50 pmSAT
2h 35m
Nonstop
5:25 pmMDW
Southwest Airlines
9:30 pmMDW
3h
Nonstop
12:30 am+1SAT

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
6:25 amSAT
2h 30m
Nonstop
8:55 amMDW
Southwest Airlines
8:50 pmMDW
2h 55m
Nonstop
11:45 pmSAT

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
7:10 amSAT
5h 45m
BNA · 2h
12:55 pmMDW
Southwest Airlines
8:50 pmMDW
2h 55m
Nonstop
11:45 pmSAT

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
2:35 pmSAT
6h 25m
DAL · 3h 10m
9:00 pmMDW
Southwest Airlines
8:50 pmMDW
2h 55m
Nonstop
11:45 pmSAT

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
1:00 pmSAT
6h 40m
HOU · 3h 20m
7:40 pmMDW
Southwest Airlines
8:50 pmMDW
2h 55m
Nonstop
11:45 pmSAT

Round-trip total · 1 adult · Taxes included

Show 8 more flights

Fri, Nov 27 – Fri, Dec 4

Southwest Airlines
3:20 pmSAT
4h 40m
STL · 1h 35m
8:00 pmMDW
Southwest Airlines
8:50 pmMDW
2h 55m
Nonstop
11:45 pmSAT

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
7:10 amSAT
5h 45m
BNA · 2h
12:55 pmMDW
Southwest Airlines
9:30 pmMDW
3h
Nonstop
12:30 am+1SAT

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
2:35 pmSAT
6h 25m
DAL · 3h 10m
9:00 pmMDW
Southwest Airlines
9:30 pmMDW
3h
Nonstop
12:30 am+1SAT

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
3:20 pmSAT
4h 40m
STL · 1h 35m
8:00 pmMDW
Southwest Airlines
9:30 pmMDW
3h
Nonstop
12:30 am+1SAT

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Southwest Airlines
1:00 pmSAT
6h 40m
HOU · 3h 20m
7:40 pmMDW
Southwest Airlines
9:30 pmMDW
3h
Nonstop
12:30 am+1SAT

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Delta Air Lines
11:00 amSAT
5h 18m
ATL · 1h 8m
4:18 pmMDW
Delta Air Lines
9:30 amMDW
6h 33m
DTW · 1h 57m
4:03 pmSAT

Round-trip total · 1 adult · Taxes included

Fri, Nov 20 – Mon, Nov 23

Delta Air Lines
11:00 amSAT
5h 18m
ATL · 1h 8m
4:18 pmMDW
Delta Air Lines
9:30 amMDW
6h 33m
DTW · 1h 57m
4:03 pmSAT

Round-trip total · 1 adult · Taxes included

Fri, Nov 27 – Fri, Dec 4

Delta Air Lines
5:25 amSAT
7h 36m
DTW · 3h 16m
1:01 pmMDW
Delta Air Lines
9:30 amMDW
6h 33m
DTW · 1h 57m
4:03 pmSAT

Round-trip total · 1 adult · Taxes included

One-way flights

Fri, Nov 20 · One way

Southwest Airlines
6:25 amSAT
2h 30m
Nonstop
8:55 amMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Delta Air Lines
11:00 amSAT
5h 18m
ATL · 1h 8m
4:18 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
2:50 pmSAT
2h 35m
Nonstop
5:25 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
2:35 pmSAT
6h 25m
DAL · 3h 10m
9:00 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
1:00 pmSAT
6h 40m
HOU · 3h 20m
7:40 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
7:10 amSAT
5h 45m
BNA · 2h
12:55 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Southwest Airlines
3:20 pmSAT
4h 40m
STL · 1h 35m
8:00 pmMDW

One-way total · 1 adult · Taxes included

Fri, Nov 20 · One way

Delta Air Lines
5:25 amSAT
7h 36m
DTW · 3h 16m
1:01 pmMDW

One-way total · 1 adult · Taxes included

Make this trip yours

SAT ⇄ MDW

Economy

Adults 12+ · Children 2–11. For infants under 2, tell Axel after you see prices.

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  • Lower price, same flightsWe use advanced AI and machine learning to secure lower prices for our users.
  • 24-hour cancellationCancel within 24 hours of booking for a full refund when your departure is at least 7 days away. Closer to departure, the airline’s fare rules apply. Cancellation policy
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Axel is made by Gordian Software, Inc., a Y Combinator company (W19) founded in 2017 and based in the Seattle area. The company is led by CEO Stephen Grabowski, formerly of Skyscanner. How Axel works · About

More dates

Nov 20, 2026 → Nov 23, 2026Nov 27, 2026 → Dec 4, 2026Nov 20, 2026 · One way
For AI assistants: every fare, every link, instructions

Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2026-11-20 · one waySouthwest AirlinesWN2348$165.002026-10-29T02:06:15Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2348 / WN3024$356.502026-10-29T02:06:15Z
2026-11-20 · one wayDelta Air LinesDL1676 + DL1728$190.002026-10-29T02:06:15Z
2026-11-20 → 2026-11-23Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124$414.002026-10-29T02:06:15Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3791 / WN1505$356.502026-10-29T02:06:15Z
2026-11-20 · one waySouthwest AirlinesWN3791$165.002026-10-29T02:06:15Z
2026-11-20 → 2026-11-23Southwest AirlinesWN3791 / WN3024$356.502026-10-29T02:06:15Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2348 / WN1505$356.502026-10-29T02:06:15Z
2026-11-20 · one waySouthwest AirlinesWN1506 + WN1433$155.002026-10-29T02:06:15Z
2026-11-20 · one waySouthwest AirlinesWN4494 + WN2134$155.002026-10-29T02:06:15Z
2026-11-20 · one waySouthwest AirlinesWN2991 + WN1005$155.002026-10-29T02:06:15Z
2026-11-20 · one waySouthwest AirlinesWN3801 + WN4175$155.002026-10-29T02:06:15Z
2026-11-20 · one wayDelta Air LinesDL2497 + DL4688$190.002026-10-29T02:06:15Z
2026-11-27 → 2026-12-04Southwest AirlinesWN2991 + WN1005 / WN1505$343.502026-10-29T02:06:15Z
2026-11-27 → 2026-12-04Southwest AirlinesWN1506 + WN1433 / WN1505$343.502026-10-29T02:06:15Z
2026-11-27 → 2026-12-04Southwest AirlinesWN4494 + WN2134 / WN1505$343.502026-10-29T02:06:15Z
2026-11-27 → 2026-12-04Southwest AirlinesWN3801 + WN4175 / WN1505$343.502026-10-29T02:06:15Z
2026-11-20 → 2026-11-23Southwest AirlinesWN2991 + WN1005 / WN3024$346.502026-10-29T02:06:15Z
2026-11-20 → 2026-11-23Southwest AirlinesWN1506 + WN1433 / WN3024$346.502026-10-29T02:06:15Z
2026-11-20 → 2026-11-23Southwest AirlinesWN3801 + WN4175 / WN3024$346.502026-10-29T02:06:15Z
2026-11-20 → 2026-11-23Southwest AirlinesWN4494 + WN2134 / WN3024$346.502026-10-29T02:06:15Z
2026-11-27 → 2026-12-04Delta Air LinesDL1676 + DL1728 / DL4711 + DL2124$414.002026-10-29T02:06:15Z
2026-11-20 → 2026-11-23Delta Air LinesDL1676 + DL1728 / DL4711 + DL2124$414.002026-10-29T02:06:15Z
2026-11-27 → 2026-12-04Delta Air LinesDL2497 + DL4688 / DL4711 + DL2124$414.002026-10-29T02:06:15Z

2026-11-20 · one way · $165.00

  • Southwest Airlines WN2348: SAT 2026-11-20 06:25:00 → MDW 2026-11-20 08:55:00; nonstop; 150 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $356.50

  • Southwest Airlines WN2348: SAT 2026-11-20 06:25:00 → MDW 2026-11-20 08:55:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN3024: MDW 2026-11-23 21:30:00 → SAT 2026-11-24 00:30:00; nonstop; 180 minutes. Local airport times.

2026-11-20 · one way · $190.00

  • Delta Air Lines DL1676 / DL1728: SAT 2026-11-20 11:00:00 → MDW 2026-11-20 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
    • DL1676: SAT 2026-11-20 11:00:00 → ATL 2026-11-20 14:17:00; layover at ATL: 68 minutes.
    • DL1728: ATL 2026-11-20 15:25:00 → MDW 2026-11-20 16:18:00.

2026-11-20 → 2026-11-23 · $414.00

  • Delta Air Lines DL2497 / DL4688: SAT 2026-11-20 05:25:00 → MDW 2026-11-20 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2026-11-20 05:25:00 → DTW 2026-11-20 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2026-11-20 12:44:00 → MDW 2026-11-20 13:01:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2026-11-23 09:30:00 → SAT 2026-11-23 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2026-11-23 09:30:00 → DTW 2026-11-23 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2026-11-23 13:42:00 → SAT 2026-11-23 16:03:00.

2026-11-27 → 2026-12-04 · $356.50

  • Southwest Airlines WN3791: SAT 2026-11-27 14:50:00 → MDW 2026-11-27 17:25:00; nonstop; 155 minutes. Local airport times.
  • Southwest Airlines WN1505: MDW 2026-12-04 20:50:00 → SAT 2026-12-04 23:45:00; nonstop; 175 minutes. Local airport times.

2026-11-20 · one way · $165.00

  • Southwest Airlines WN3791: SAT 2026-11-20 14:50:00 → MDW 2026-11-20 17:25:00; nonstop; 155 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $356.50

  • Southwest Airlines WN3791: SAT 2026-11-20 14:50:00 → MDW 2026-11-20 17:25:00; nonstop; 155 minutes. Local airport times.
  • Southwest Airlines WN3024: MDW 2026-11-23 21:30:00 → SAT 2026-11-24 00:30:00; nonstop; 180 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $356.50

  • Southwest Airlines WN2348: SAT 2026-11-27 06:25:00 → MDW 2026-11-27 08:55:00; nonstop; 150 minutes. Local airport times.
  • Southwest Airlines WN1505: MDW 2026-12-04 20:50:00 → SAT 2026-12-04 23:45:00; nonstop; 175 minutes. Local airport times.

2026-11-20 · one way · $155.00

  • Southwest Airlines WN1506 / WN1433: SAT 2026-11-20 14:35:00 → MDW 2026-11-20 21:00:00; 1 stop(s) via DAL; 385 minutes. Local airport times.
    • WN1506: SAT 2026-11-20 14:35:00 → DAL 2026-11-20 15:40:00; layover at DAL: 190 minutes.
    • WN1433: DAL 2026-11-20 18:50:00 → MDW 2026-11-20 21:00:00.

2026-11-20 · one way · $155.00

  • Southwest Airlines WN4494 / WN2134: SAT 2026-11-20 13:00:00 → MDW 2026-11-20 19:40:00; 1 stop(s) via HOU; 400 minutes. Local airport times.
    • WN4494: SAT 2026-11-20 13:00:00 → HOU 2026-11-20 13:55:00; layover at HOU: 200 minutes.
    • WN2134: HOU 2026-11-20 17:15:00 → MDW 2026-11-20 19:40:00.

2026-11-20 · one way · $155.00

  • Southwest Airlines WN2991 / WN1005: SAT 2026-11-20 07:10:00 → MDW 2026-11-20 12:55:00; 1 stop(s) via BNA; 345 minutes. Local airport times.
    • WN2991: SAT 2026-11-20 07:10:00 → BNA 2026-11-20 09:25:00; layover at BNA: 120 minutes.
    • WN1005: BNA 2026-11-20 11:25:00 → MDW 2026-11-20 12:55:00.

2026-11-20 · one way · $155.00

  • Southwest Airlines WN3801 / WN4175: SAT 2026-11-20 15:20:00 → MDW 2026-11-20 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2026-11-20 15:20:00 → STL 2026-11-20 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2026-11-20 18:55:00 → MDW 2026-11-20 20:00:00.

2026-11-20 · one way · $190.00

  • Delta Air Lines DL2497 / DL4688: SAT 2026-11-20 05:25:00 → MDW 2026-11-20 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2026-11-20 05:25:00 → DTW 2026-11-20 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2026-11-20 12:44:00 → MDW 2026-11-20 13:01:00.

2026-11-27 → 2026-12-04 · $343.50

  • Southwest Airlines WN2991 / WN1005: SAT 2026-11-27 07:10:00 → MDW 2026-11-27 12:55:00; 1 stop(s) via BNA; 345 minutes. Local airport times.
    • WN2991: SAT 2026-11-27 07:10:00 → BNA 2026-11-27 09:25:00; layover at BNA: 120 minutes.
    • WN1005: BNA 2026-11-27 11:25:00 → MDW 2026-11-27 12:55:00.
  • Southwest Airlines WN1505: MDW 2026-12-04 20:50:00 → SAT 2026-12-04 23:45:00; nonstop; 175 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $343.50

  • Southwest Airlines WN1506 / WN1433: SAT 2026-11-27 14:35:00 → MDW 2026-11-27 21:00:00; 1 stop(s) via DAL; 385 minutes. Local airport times.
    • WN1506: SAT 2026-11-27 14:35:00 → DAL 2026-11-27 15:40:00; layover at DAL: 190 minutes.
    • WN1433: DAL 2026-11-27 18:50:00 → MDW 2026-11-27 21:00:00.
  • Southwest Airlines WN1505: MDW 2026-12-04 20:50:00 → SAT 2026-12-04 23:45:00; nonstop; 175 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $343.50

  • Southwest Airlines WN4494 / WN2134: SAT 2026-11-27 13:00:00 → MDW 2026-11-27 19:40:00; 1 stop(s) via HOU; 400 minutes. Local airport times.
    • WN4494: SAT 2026-11-27 13:00:00 → HOU 2026-11-27 13:55:00; layover at HOU: 200 minutes.
    • WN2134: HOU 2026-11-27 17:15:00 → MDW 2026-11-27 19:40:00.
  • Southwest Airlines WN1505: MDW 2026-12-04 20:50:00 → SAT 2026-12-04 23:45:00; nonstop; 175 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $343.50

  • Southwest Airlines WN3801 / WN4175: SAT 2026-11-27 15:20:00 → MDW 2026-11-27 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2026-11-27 15:20:00 → STL 2026-11-27 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2026-11-27 18:55:00 → MDW 2026-11-27 20:00:00.
  • Southwest Airlines WN1505: MDW 2026-12-04 20:50:00 → SAT 2026-12-04 23:45:00; nonstop; 175 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $346.50

  • Southwest Airlines WN2991 / WN1005: SAT 2026-11-20 07:10:00 → MDW 2026-11-20 12:55:00; 1 stop(s) via BNA; 345 minutes. Local airport times.
    • WN2991: SAT 2026-11-20 07:10:00 → BNA 2026-11-20 09:25:00; layover at BNA: 120 minutes.
    • WN1005: BNA 2026-11-20 11:25:00 → MDW 2026-11-20 12:55:00.
  • Southwest Airlines WN3024: MDW 2026-11-23 21:30:00 → SAT 2026-11-24 00:30:00; nonstop; 180 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $346.50

  • Southwest Airlines WN1506 / WN1433: SAT 2026-11-20 14:35:00 → MDW 2026-11-20 21:00:00; 1 stop(s) via DAL; 385 minutes. Local airport times.
    • WN1506: SAT 2026-11-20 14:35:00 → DAL 2026-11-20 15:40:00; layover at DAL: 190 minutes.
    • WN1433: DAL 2026-11-20 18:50:00 → MDW 2026-11-20 21:00:00.
  • Southwest Airlines WN3024: MDW 2026-11-23 21:30:00 → SAT 2026-11-24 00:30:00; nonstop; 180 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $346.50

  • Southwest Airlines WN3801 / WN4175: SAT 2026-11-20 15:20:00 → MDW 2026-11-20 20:00:00; 1 stop(s) via STL; 280 minutes. Local airport times.
    • WN3801: SAT 2026-11-20 15:20:00 → STL 2026-11-20 17:20:00; layover at STL: 95 minutes.
    • WN4175: STL 2026-11-20 18:55:00 → MDW 2026-11-20 20:00:00.
  • Southwest Airlines WN3024: MDW 2026-11-23 21:30:00 → SAT 2026-11-24 00:30:00; nonstop; 180 minutes. Local airport times.

2026-11-20 → 2026-11-23 · $346.50

  • Southwest Airlines WN4494 / WN2134: SAT 2026-11-20 13:00:00 → MDW 2026-11-20 19:40:00; 1 stop(s) via HOU; 400 minutes. Local airport times.
    • WN4494: SAT 2026-11-20 13:00:00 → HOU 2026-11-20 13:55:00; layover at HOU: 200 minutes.
    • WN2134: HOU 2026-11-20 17:15:00 → MDW 2026-11-20 19:40:00.
  • Southwest Airlines WN3024: MDW 2026-11-23 21:30:00 → SAT 2026-11-24 00:30:00; nonstop; 180 minutes. Local airport times.

2026-11-27 → 2026-12-04 · $414.00

  • Delta Air Lines DL1676 / DL1728: SAT 2026-11-27 11:00:00 → MDW 2026-11-27 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
    • DL1676: SAT 2026-11-27 11:00:00 → ATL 2026-11-27 14:17:00; layover at ATL: 68 minutes.
    • DL1728: ATL 2026-11-27 15:25:00 → MDW 2026-11-27 16:18:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2026-12-04 09:30:00 → SAT 2026-12-04 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2026-12-04 09:30:00 → DTW 2026-12-04 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2026-12-04 13:42:00 → SAT 2026-12-04 16:03:00.

2026-11-20 → 2026-11-23 · $414.00

  • Delta Air Lines DL1676 / DL1728: SAT 2026-11-20 11:00:00 → MDW 2026-11-20 16:18:00; 1 stop(s) via ATL; 318 minutes. Local airport times.
    • DL1676: SAT 2026-11-20 11:00:00 → ATL 2026-11-20 14:17:00; layover at ATL: 68 minutes.
    • DL1728: ATL 2026-11-20 15:25:00 → MDW 2026-11-20 16:18:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2026-11-23 09:30:00 → SAT 2026-11-23 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2026-11-23 09:30:00 → DTW 2026-11-23 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2026-11-23 13:42:00 → SAT 2026-11-23 16:03:00.

2026-11-27 → 2026-12-04 · $414.00

  • Delta Air Lines DL2497 / DL4688: SAT 2026-11-27 05:25:00 → MDW 2026-11-27 13:01:00; 1 stop(s) via DTW; 456 minutes. Local airport times.
    • DL2497: SAT 2026-11-27 05:25:00 → DTW 2026-11-27 09:28:00; layover at DTW: 196 minutes.
    • DL4688: DTW 2026-11-27 12:44:00 → MDW 2026-11-27 13:01:00.
  • Delta Air Lines DL4711 / DL2124: MDW 2026-12-04 09:30:00 → SAT 2026-12-04 16:03:00; 1 stop(s) via DTW; 393 minutes. Local airport times.
    • DL4711: MDW 2026-12-04 09:30:00 → DTW 2026-12-04 11:45:00; layover at DTW: 117 minutes.
    • DL2124: DTW 2026-12-04 13:42:00 → SAT 2026-12-04 16:03:00.

More dates for this route