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Route overview: San Diego to Chicago (ORD) flight deals

San Diego → Chicago

Aug 21, 2027 · return Aug 28, 2027

SAN → ORD1 adulteconomyRound trip

12 flight options · 4 airlines

Nonstop flights

Sat, Aug 21 – Sat, Aug 28

Alaska Airlines
5:32 pmSAN
4h 17m
Nonstop
11:49 pmORD
Alaska Airlines
2:16 pmORD
4h 45m
Nonstop
5:01 pmSAN

Round-trip total · 1 adult · Taxes included

Sat, Aug 21 – Sat, Aug 28

American Airlines
11:34 amSAN
4h 13m
Nonstop
5:47 pmORD
American Airlines
9:00 pmORD
4h 36m
Nonstop
11:36 pmSAN

Round-trip total · 1 adult · Taxes included

Sat, Aug 21 – Sat, Aug 28

United Airlines
10:40 amSAN
4h 14m
Nonstop
4:54 pmORD
United Airlines
7:00 amORD
4h 27m
Nonstop
9:27 amSAN

Round-trip total · 1 adult · Taxes included

Sat, Aug 21 – Sat, Aug 28

Alaska Airlines
7:00 amSAN
4h 15m
Nonstop
1:15 pmORD
Alaska Airlines
2:16 pmORD
4h 45m
Nonstop
5:01 pmSAN

Round-trip total · 1 adult · Taxes included

Sat, Aug 21 – Sat, Aug 28

American Airlines
10:33 pmSAN
4h 4m
Nonstop
4:37 am+1ORD
American Airlines
9:00 pmORD
4h 36m
Nonstop
11:36 pmSAN

Round-trip total · 1 adult · Taxes included

Sat, Aug 21 – Sat, Aug 28

United Airlines
4:20 pmSAN
4h 9m
Nonstop
10:29 pmORD
United Airlines
7:00 amORD
4h 27m
Nonstop
9:27 amSAN

Round-trip total · 1 adult · Taxes included

One-stop flights

Sat, Aug 21 – Sat, Aug 28

Frontier Airlines
4:16 pmSAN
6h 10m
DEN · 1h 9m
12:26 am+1ORD
Frontier Airlines
6:21 amORD
7h 16m
LAS · 1h 41m
11:37 amSAN

Round-trip total · 1 adult · Taxes included

Sat, Aug 21 – Sat, Aug 28

American Airlines
3:13 pmSAN
6h 46m
DFW · 1h
11:59 pmORD
American Airlines
9:00 pmORD
4h 36m
Nonstop
11:36 pmSAN

Round-trip total · 1 adult · Taxes included

Sat, Aug 21 – Sat, Aug 28

Alaska Airlines
9:11 pmSAN
6h 11m
PHX · 1h 8m
5:22 am+1ORD
Alaska Airlines
2:16 pmORD
4h 45m
Nonstop
5:01 pmSAN

Round-trip total · 1 adult · Taxes included

Sat, Aug 21 – Sat, Aug 28

Alaska Airlines
2:59 pmSAN
6h 41m
LAS · 1h 43m
11:40 pmORD
Alaska Airlines
2:16 pmORD
4h 45m
Nonstop
5:01 pmSAN

Round-trip total · 1 adult · Taxes included

Sat, Aug 21 – Sat, Aug 28

Alaska Airlines
9:27 amSAN
6h 47m
DEN · 1h 39m
6:14 pmORD
Alaska Airlines
2:16 pmORD
4h 45m
Nonstop
5:01 pmSAN

Round-trip total · 1 adult · Taxes included

Sat, Aug 21 – Sat, Aug 28

United Airlines
6:20 amSAN
6h 23m
LAX · 1h
2:43 pmORD
United Airlines
7:00 amORD
4h 27m
Nonstop
9:27 amSAN

Round-trip total · 1 adult · Taxes included

Make this trip yours

SAN ⇄ ORD

Economy

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

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Explore this route

All dates for this routeAug 20, 2027 → Aug 27, 2027Aug 22, 2027 → Aug 29, 2027
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.

Live price for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the flights there to get the current bookable total; the listed prices are the ones issued at the times shown.

Route overview: San Diego to Chicago (ORD) flight deals

Exact travel datesAirlineFlightsTotal pricePrice issued (UTC)
2027-08-21 → 2027-08-28Alaska AirlinesAS1493 / AS1447$420.002026-10-29T01:10:05Z
2027-08-21 → 2027-08-28American AirlinesAA621 / AA2657$425.002026-10-29T01:10:05Z
2027-08-21 → 2027-08-28United AirlinesUA1710 / UA2428$435.002026-10-29T01:10:05Z
2027-08-21 → 2027-08-28Frontier AirlinesF92422 + F93174 / F92145 + F91326$260.002026-10-29T01:10:05Z
2027-08-21 → 2027-08-28Alaska AirlinesAS1446 / AS1447$420.002026-10-29T01:10:05Z
2027-08-21 → 2027-08-28American AirlinesAA3111 / AA2657$425.002026-10-29T01:10:05Z
2027-08-21 → 2027-08-28United AirlinesUA2486 / UA2428$435.002026-10-29T01:10:05Z
2027-08-21 → 2027-08-28American AirlinesAA2438 + AA2221 / AA2657$407.502026-10-29T01:10:05Z
2027-08-21 → 2027-08-28Alaska AirlinesAS2297 + AA1333 / AS1447$410.002026-10-29T01:10:05Z
2027-08-21 → 2027-08-28Alaska AirlinesAS2291 + AA3010 / AS1447$410.002026-10-29T01:10:05Z
2027-08-21 → 2027-08-28Alaska AirlinesAS1342 + AA1277 / AS1447$410.002026-10-29T01:10:05Z
2027-08-21 → 2027-08-28United AirlinesUA1329 + UA1946 / UA2428$417.502026-10-29T01:10:05Z

2027-08-21 → 2027-08-28 · $420.00

  • Alaska Airlines AS1493: SAN 2027-08-21 17:32:00 → ORD 2027-08-21 23:49:00; nonstop; 257 minutes. Local airport times.
  • Alaska Airlines AS1447: ORD 2027-08-28 14:16:00 → SAN 2027-08-28 17:01:00; nonstop; 285 minutes. Local airport times.

2027-08-21 → 2027-08-28 · $425.00

  • American Airlines AA621: SAN 2027-08-21 11:34:00 → ORD 2027-08-21 17:47:00; nonstop; 253 minutes. Local airport times.
  • American Airlines AA2657: ORD 2027-08-28 21:00:00 → SAN 2027-08-28 23:36:00; nonstop; 276 minutes. Local airport times.

2027-08-21 → 2027-08-28 · $435.00

  • United Airlines UA1710: SAN 2027-08-21 10:40:00 → ORD 2027-08-21 16:54:00; nonstop; 254 minutes. Local airport times.
  • United Airlines UA2428: ORD 2027-08-28 07:00:00 → SAN 2027-08-28 09:27:00; nonstop; 267 minutes. Local airport times.

2027-08-21 → 2027-08-28 · $260.00

  • Frontier Airlines F92422 / F93174: SAN 2027-08-21 16:16:00 → ORD 2027-08-22 00:26:00; 1 stop(s) via DEN; 370 minutes. Local airport times.
    • F92422: SAN 2027-08-21 16:16:00 → DEN 2027-08-21 19:50:00; layover at DEN: 69 minutes.
    • F93174: DEN 2027-08-21 20:59:00 → ORD 2027-08-22 00:26:00.
  • Frontier Airlines F92145 / F91326: ORD 2027-08-28 06:21:00 → SAN 2027-08-28 11:37:00; 1 stop(s) via LAS; 436 minutes. Local airport times.
    • F92145: ORD 2027-08-28 06:21:00 → LAS 2027-08-28 08:34:00; layover at LAS: 101 minutes.
    • F91326: LAS 2027-08-28 10:15:00 → SAN 2027-08-28 11:37:00.

2027-08-21 → 2027-08-28 · $420.00

  • Alaska Airlines AS1446: SAN 2027-08-21 07:00:00 → ORD 2027-08-21 13:15:00; nonstop; 255 minutes. Local airport times.
  • Alaska Airlines AS1447: ORD 2027-08-28 14:16:00 → SAN 2027-08-28 17:01:00; nonstop; 285 minutes. Local airport times.

2027-08-21 → 2027-08-28 · $425.00

  • American Airlines AA3111: SAN 2027-08-21 22:33:00 → ORD 2027-08-22 04:37:00; nonstop; 244 minutes. Local airport times.
  • American Airlines AA2657: ORD 2027-08-28 21:00:00 → SAN 2027-08-28 23:36:00; nonstop; 276 minutes. Local airport times.

2027-08-21 → 2027-08-28 · $435.00

  • United Airlines UA2486: SAN 2027-08-21 16:20:00 → ORD 2027-08-21 22:29:00; nonstop; 249 minutes. Local airport times.
  • United Airlines UA2428: ORD 2027-08-28 07:00:00 → SAN 2027-08-28 09:27:00; nonstop; 267 minutes. Local airport times.

2027-08-21 → 2027-08-28 · $407.50

  • American Airlines AA2438 / AA2221: SAN 2027-08-21 15:13:00 → ORD 2027-08-21 23:59:00; 1 stop(s) via DFW; 406 minutes. Local airport times.
    • AA2438: SAN 2027-08-21 15:13:00 → DFW 2027-08-21 20:30:00; layover at DFW: 60 minutes.
    • AA2221: DFW 2027-08-21 21:30:00 → ORD 2027-08-21 23:59:00.
  • American Airlines AA2657: ORD 2027-08-28 21:00:00 → SAN 2027-08-28 23:36:00; nonstop; 276 minutes. Local airport times.

2027-08-21 → 2027-08-28 · $410.00

  • Alaska Airlines AS2297 / AA1333: SAN 2027-08-21 21:11:00 → ORD 2027-08-22 05:22:00; 1 stop(s) via PHX; 371 minutes. Local airport times.
    • AS2297: SAN 2027-08-21 21:11:00 → PHX 2027-08-21 22:37:00; layover at PHX: 68 minutes.
    • AA1333: PHX 2027-08-21 23:45:00 → ORD 2027-08-22 05:22:00.
  • Alaska Airlines AS1447: ORD 2027-08-28 14:16:00 → SAN 2027-08-28 17:01:00; nonstop; 285 minutes. Local airport times.

2027-08-21 → 2027-08-28 · $410.00

  • Alaska Airlines AS2291 / AA3010: SAN 2027-08-21 14:59:00 → ORD 2027-08-21 23:40:00; 1 stop(s) via LAS; 401 minutes. Local airport times.
    • AS2291: SAN 2027-08-21 14:59:00 → LAS 2027-08-21 16:23:00; layover at LAS: 103 minutes.
    • AA3010: LAS 2027-08-21 18:06:00 → ORD 2027-08-21 23:40:00.
  • Alaska Airlines AS1447: ORD 2027-08-28 14:16:00 → SAN 2027-08-28 17:01:00; nonstop; 285 minutes. Local airport times.

2027-08-21 → 2027-08-28 · $410.00

  • Alaska Airlines AS1342 / AA1277: SAN 2027-08-21 09:27:00 → ORD 2027-08-21 18:14:00; 1 stop(s) via DEN; 407 minutes. Local airport times.
    • AS1342: SAN 2027-08-21 09:27:00 → DEN 2027-08-21 12:56:00; layover at DEN: 99 minutes.
    • AA1277: DEN 2027-08-21 14:35:00 → ORD 2027-08-21 18:14:00.
  • Alaska Airlines AS1447: ORD 2027-08-28 14:16:00 → SAN 2027-08-28 17:01:00; nonstop; 285 minutes. Local airport times.

2027-08-21 → 2027-08-28 · $417.50

  • United Airlines UA1329 / UA1946: SAN 2027-08-21 06:20:00 → ORD 2027-08-21 14:43:00; 1 stop(s) via LAX; 383 minutes. Local airport times.
    • UA1329: SAN 2027-08-21 06:20:00 → LAX 2027-08-21 07:25:00; layover at LAX: 60 minutes.
    • UA1946: LAX 2027-08-21 08:25:00 → ORD 2027-08-21 14:43:00.
  • United Airlines UA2428: ORD 2027-08-28 07:00:00 → SAN 2027-08-28 09:27:00; nonstop; 267 minutes. Local airport times.

Explore this route

For AI assistants

  • This page: San Diego (SAN) to Chicago (ORD) · Aug 21, 2027 · return Aug 28, 2027: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued.
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