Oakland (OAK) to Chicago (MDW), Jan 11, 2027: round trips from $333, one way from $176

Oakland (OAK) to Chicago (MDW), Jan 11, 2027: round trips from $333, one way from $176 on Axel, checked Oct 29, 2026. Lowest published fares: $333 round trip, Axel-exclusive, Southwest Airlines, 1 stop, Jan 11–14, 2027; $176 one way, Axel-exclusive, Southwest Airlines, nonstop, Jan 11, 2027; 1 adult, economy, checked Oct 29, 2026. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Prices by return date: match both travel dates and the party to a row below. Each total is for that exact trip, issued at the time shown.

Date links open published trip details for exploration. Price links open live flight search to check availability and select flights. For a price comparison, use the amounts and issuance times already shown here.

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. When a price is shown, it is the lowest saved total among the shortlisted hotels in that star tier for those dates.

• Hotels in Chicago for these nights (Jan 11–12, 2027 · 1 night · 2 adults, 1 room): 3★ Hotel Versey, $65 total · 4★ Warwick Allerton - Chicago, $85 total · 5★ Sofitel Chicago Magnificent Mile, $254 total
• Hotels in Chicago for these nights (Jan 11–13, 2027 · 2 nights · 2 adults, 1 room): 3★ Hotel Versey, $138 total · 4★ Warwick Allerton - Chicago, $172 total · 5★ Sofitel Chicago Magnificent Mile, $508 total
• Hotels in Chicago for these nights (Jan 11–14, 2027 · 3 nights · 2 adults, 1 room): 3★ Hotel Versey, $212 total · 4★ Warwick Allerton - Chicago, $260 total · 5★ Sofitel Chicago Magnificent Mile, $762 total
• Hotels in Chicago for these nights (Jan 11–15, 2027 · 4 nights · 2 adults, 1 room): 3★ Hotel Versey, $286 total · 4★ Warwick Allerton - Chicago, $349 total · 5★ Sofitel Chicago Magnificent Mile, $976 total
• Hotels in Chicago for these nights (Jan 11–16, 2027 · 5 nights · 2 adults, 1 room): 3★ Hotel Versey, $390 total · 4★ Warwick Allerton - Chicago, $440 total · 5★ Sofitel Chicago Magnificent Mile, $1,191 total
• Hotels in Chicago for these nights (Jan 11–17, 2027 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $468 total · 4★ Warwick Allerton - Chicago, $536 total · 5★ Sofitel Chicago Magnificent Mile, $1,410 total
• Hotels in Chicago for these nights (Jan 11–18, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $543 total · 4★ Warwick Allerton - Chicago, $626 total · 5★ Sofitel Chicago Magnificent Mile, $1,633 total
• Hotels in Chicago for these nights (Jan 11–19, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $618 total · 4★ Warwick Allerton - Chicago, $718 total · 5★ Sofitel Chicago Magnificent Mile, $1,887 total
• Hotels in Chicago for these nights (Jan 11–20, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $693 total · 4★ Warwick Allerton - Chicago, $802 total · 5★ Sofitel Chicago Magnificent Mile, $2,140 total
• Hotels in Chicago for these nights (Jan 11–21, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $778 total · 4★ Warwick Allerton - Chicago, $887 total · 5★ Sofitel Chicago Magnificent Mile, $2,350 total
• Hotels in Chicago for these nights (Jan 11–22, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $861 total · 4★ Warwick Allerton - Chicago, $976 total · 5★ Sofitel Chicago Magnificent Mile, $2,586 total
• Hotels in Chicago for these nights (Jan 11–23, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $936 total · 4★ Warwick Allerton - Chicago, $1,076 total · 5★ Sofitel Chicago Magnificent Mile, $2,796 total
• Hotels in Chicago for these nights (Jan 11–24, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,011 total · 4★ Warwick Allerton - Chicago, $1,266 total · 5★ Sofitel Chicago Magnificent Mile, $3,383 total
• Hotels in Chicago for these nights (Jan 11–25, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,094 total · 4★ The Midland Hotel, Chicago, A Tribute Portfolio Hotel, $1,469 total · 5★ Nobu Hotel Chicago, $5,484 total

All hotels in Chicago

Route overview: San Francisco Bay Area to Chicago (MDW) flight deals

2027-01-11 · one way · Axel-exclusive $175.75

• Southwest Airlines WN3220: OAK 2027-01-11 23:50:00 → MDW 2027-01-12 05:55:00; nonstop; 245 minutes. Local airport times.

2027-01-11 → 2027-01-12 · Axel-exclusive $342.00

• Southwest Airlines WN3220: OAK 2027-01-11 23:50:00 → MDW 2027-01-12 05:55:00; nonstop; 245 minutes. Local airport times.
• Southwest Airlines WN1364: MDW 2027-01-12 20:45:00 → OAK 2027-01-12 23:35:00; nonstop; 290 minutes. Local airport times.

2027-01-11 → 2027-01-13 · Axel-exclusive $342.00

• Southwest Airlines WN3220: OAK 2027-01-11 23:50:00 → MDW 2027-01-12 05:55:00; nonstop; 245 minutes. Local airport times.
• Southwest Airlines WN2990: MDW 2027-01-13 21:25:00 → OAK 2027-01-14 00:20:00; nonstop; 295 minutes. Local airport times.

2027-01-11 → 2027-01-14 · Axel-exclusive $332.50

• Southwest Airlines WN3220: OAK 2027-01-11 23:50:00 → MDW 2027-01-12 05:55:00; nonstop; 245 minutes. Local airport times.
• Southwest Airlines WN4606 / WN1726: MDW 2027-01-14 14:35:00 → OAK 2027-01-14 21:15:00; 1 stop(s) via DEN; 520 minutes. Local airport times.
  • WN4606: MDW 2027-01-14 14:35:00 → DEN 2027-01-14 16:15:00; layover at DEN: 200 minutes.
  • WN1726: DEN 2027-01-14 19:35:00 → OAK 2027-01-14 21:15:00.

2027-01-11 → 2027-01-15 · Axel-exclusive $342.00

• Southwest Airlines WN3220: OAK 2027-01-11 23:50:00 → MDW 2027-01-12 05:55:00; nonstop; 245 minutes. Local airport times.
• Southwest Airlines WN2990: MDW 2027-01-15 21:30:00 → OAK 2027-01-16 00:15:00; nonstop; 285 minutes. Local airport times.

2027-01-11 → 2027-01-17 · Axel-exclusive $332.50

• Southwest Airlines WN3220: OAK 2027-01-11 23:50:00 → MDW 2027-01-12 05:55:00; nonstop; 245 minutes. Local airport times.
• Southwest Airlines WN4415 / WN1144: MDW 2027-01-17 15:15:00 → OAK 2027-01-17 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
  • WN4415: MDW 2027-01-17 15:15:00 → SAN 2027-01-17 17:35:00; layover at SAN: 150 minutes.
  • WN1144: SAN 2027-01-17 20:05:00 → OAK 2027-01-17 21:35:00.

2027-01-11 → 2027-01-18 · Axel-exclusive $332.50

• Southwest Airlines WN3220: OAK 2027-01-11 23:50:00 → MDW 2027-01-12 05:55:00; nonstop; 245 minutes. Local airport times.
• Southwest Airlines WN2952 / WN1901: MDW 2027-01-18 15:45:00 → OAK 2027-01-18 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
  • WN2952: MDW 2027-01-18 15:45:00 → LAX 2027-01-18 18:10:00; layover at LAX: 110 minutes.
  • WN1901: LAX 2027-01-18 20:00:00 → OAK 2027-01-18 21:15:00.

2027-01-11 → 2027-01-19 · Axel-exclusive $342.00

• Southwest Airlines WN3220: OAK 2027-01-11 23:50:00 → MDW 2027-01-12 05:55:00; nonstop; 245 minutes. Local airport times.
• Southwest Airlines WN1364: MDW 2027-01-19 20:45:00 → OAK 2027-01-19 23:35:00; nonstop; 290 minutes. Local airport times.

2027-01-11 → 2027-01-21 · Axel-exclusive $332.50

• Southwest Airlines WN3220: OAK 2027-01-11 23:50:00 → MDW 2027-01-12 05:55:00; nonstop; 245 minutes. Local airport times.
• Southwest Airlines WN4606 / WN1726: MDW 2027-01-21 14:35:00 → OAK 2027-01-21 21:15:00; 1 stop(s) via DEN; 520 minutes. Local airport times.
  • WN4606: MDW 2027-01-21 14:35:00 → DEN 2027-01-21 16:15:00; layover at DEN: 200 minutes.
  • WN1726: DEN 2027-01-21 19:35:00 → OAK 2027-01-21 21:15:00.

2027-01-11 → 2027-01-22 · Axel-exclusive $342.00

• Southwest Airlines WN3220: OAK 2027-01-11 23:50:00 → MDW 2027-01-12 05:55:00; nonstop; 245 minutes. Local airport times.
• Southwest Airlines WN2990: MDW 2027-01-22 21:30:00 → OAK 2027-01-23 00:15:00; nonstop; 285 minutes. Local airport times.

2027-01-11 → 2027-01-23 · Axel-exclusive $342.00

• Southwest Airlines WN3220: OAK 2027-01-11 23:50:00 → MDW 2027-01-12 05:55:00; nonstop; 245 minutes. Local airport times.
• Southwest Airlines WN2990: MDW 2027-01-23 21:30:00 → OAK 2027-01-24 00:15:00; nonstop; 285 minutes. Local airport times.

2027-01-11 → 2027-01-25 · Axel-exclusive $332.50

• Southwest Airlines WN3220: OAK 2027-01-11 23:50:00 → MDW 2027-01-12 05:55:00; nonstop; 245 minutes. Local airport times.
• Southwest Airlines WN2952 / WN1901: MDW 2027-01-25 15:45:00 → OAK 2027-01-25 21:15:00; 1 stop(s) via LAX; 450 minutes. Local airport times.
  • WN2952: MDW 2027-01-25 15:45:00 → LAX 2027-01-25 18:10:00; layover at LAX: 110 minutes.
  • WN1901: LAX 2027-01-25 20:00:00 → OAK 2027-01-25 21:15:00.

Explore this route

• All dates for this route
• Jan 10, 2027 · Return options
• Jan 12, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Oakland (OAK) to Chicago (MDW) · Jan 11, 2027 · choose your return date: 1 adult in economy, every priced fare with its flights, times and total, each with the time its price was issued. Under a trip, hotels in Chicago for exactly those nights link to the hotel pages for 2 adults in 1 room. Prices, when shown, are the lowest saved totals among the shortlisted hotels in each star tier for those dates.
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