Oakland (OAK) to Chicago (MDW), Jan 10, 2027: round trips from $333, one way from $176

Oakland (OAK) to Chicago (MDW), Jan 10, 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 10–11, 2027; $176 one way, Axel-exclusive, Southwest Airlines, nonstop, Jan 10, 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 10–11, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $73 total · 4★ Freehand Chicago, $70 total · 5★ Sofitel Chicago Magnificent Mile, $219 total
• Hotels in Chicago for these nights (Jan 10–12, 2027 · 2 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $158 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $125 total · 5★ Sofitel Chicago Magnificent Mile, $425 total
• Hotels in Chicago for these nights (Jan 10–13, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $231 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $196 total · 5★ Sofitel Chicago Magnificent Mile, $635 total
• Hotels in Chicago for these nights (Jan 10–14, 2027 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $304 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $215 total · 5★ Sofitel Chicago Magnificent Mile, $834 total
• Hotels in Chicago for these nights (Jan 10–15, 2027 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $377 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $234 total · 5★ Sofitel Chicago Magnificent Mile, $1,044 total
• Hotels in Chicago for these nights (Jan 10–16, 2027 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $447 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $260 total · 5★ Sofitel Chicago Magnificent Mile, $1,302 total
• Hotels in Chicago for these nights (Jan 10–17, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $520 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $286 total · 5★ Sofitel Chicago Magnificent Mile, $1,560 total
• Hotels in Chicago for these nights (Jan 10–18, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $601 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $305 total · 5★ Sofitel Chicago Magnificent Mile, $1,766 total
• Hotels in Chicago for these nights (Jan 10–19, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $674 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $376 total · 5★ Sofitel Chicago Magnificent Mile, $1,993 total
• Hotels in Chicago for these nights (Jan 10–20, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $758 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $447 total · 5★ Sofitel Chicago Magnificent Mile, $2,199 total
• Hotels in Chicago for these nights (Jan 10–21, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $843 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $518 total · 5★ Sofitel Chicago Magnificent Mile, $2,457 total
• Hotels in Chicago for these nights (Jan 10–22, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $916 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $537 total · 5★ Sofitel Chicago Magnificent Mile, $2,666 total
• Hotels in Chicago for these nights (Jan 10–23, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $989 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $634 total · 5★ Sofitel Chicago Magnificent Mile, $2,915 total
• Hotels in Chicago for these nights (Jan 10–24, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,062 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $731 total · 5★ Sofitel Chicago Magnificent Mile, $3,502 total

All hotels in Chicago

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

2027-01-10 · one way · Axel-exclusive $175.75

• Southwest Airlines WN3220: OAK 2027-01-10 23:50:00 → MDW 2027-01-11 05:55:00; nonstop; 245 minutes. Local airport times.

2027-01-10 → 2027-01-11 · Axel-exclusive $332.50

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

2027-01-10 → 2027-01-12 · Axel-exclusive $342.00

• Southwest Airlines WN3220: OAK 2027-01-10 23:50:00 → MDW 2027-01-11 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.

2027-01-10 → 2027-01-13 · Axel-exclusive $342.00

• Southwest Airlines WN3220: OAK 2027-01-10 23:50:00 → MDW 2027-01-11 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.

2027-01-10 → 2027-01-14 · Axel-exclusive $332.50

• Southwest Airlines WN3220: OAK 2027-01-10 23:50:00 → MDW 2027-01-11 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.

2027-01-10 → 2027-01-16 · Axel-exclusive $342.00

• Southwest Airlines WN3220: OAK 2027-01-10 23:50:00 → MDW 2027-01-11 05:55:00; nonstop; 245 minutes. Local airport times.
• Southwest Airlines WN2990: MDW 2027-01-16 21:30:00 → OAK 2027-01-17 00:15:00; nonstop; 285 minutes. Local airport times.

2027-01-10 → 2027-01-17 · Axel-exclusive $332.50

• Southwest Airlines WN3220: OAK 2027-01-10 23:50:00 → MDW 2027-01-11 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.

2027-01-10 → 2027-01-18 · Axel-exclusive $332.50

• Southwest Airlines WN3220: OAK 2027-01-10 23:50:00 → MDW 2027-01-11 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.

2027-01-10 → 2027-01-20 · Axel-exclusive $342.00

• Southwest Airlines WN3220: OAK 2027-01-10 23:50:00 → MDW 2027-01-11 05:55:00; nonstop; 245 minutes. Local airport times.
• Southwest Airlines WN2990: MDW 2027-01-20 21:25:00 → OAK 2027-01-21 00:20:00; nonstop; 295 minutes. Local airport times.

2027-01-10 → 2027-01-21 · Axel-exclusive $332.50

• Southwest Airlines WN3220: OAK 2027-01-10 23:50:00 → MDW 2027-01-11 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.

2027-01-10 → 2027-01-22 · Axel-exclusive $342.00

• Southwest Airlines WN3220: OAK 2027-01-10 23:50:00 → MDW 2027-01-11 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.

2027-01-10 → 2027-01-24 · Axel-exclusive $332.50

• Southwest Airlines WN3220: OAK 2027-01-10 23:50:00 → MDW 2027-01-11 05:55:00; nonstop; 245 minutes. Local airport times.
• Southwest Airlines WN4415 / WN1144: MDW 2027-01-24 15:15:00 → OAK 2027-01-24 21:35:00; 1 stop(s) via SAN; 500 minutes. Local airport times.
  • WN4415: MDW 2027-01-24 15:15:00 → SAN 2027-01-24 17:35:00; layover at SAN: 150 minutes.
  • WN1144: SAN 2027-01-24 20:05:00 → OAK 2027-01-24 21:35:00.

Explore this route

• All dates for this route
• Jan 9, 2027 · Return options
• Jan 11, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Oakland (OAK) to Chicago (MDW) · Jan 10, 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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