Flights to Chicago (MDW): deals from 12 cities
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Flights to Chicago (MDW) by departure city
- Seattle to Chicago (MDW)
- New York to Chicago (MDW)
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Fares observed October 22 – 27, 2026. USD for the travelers shown. Search a trip for current prices.
November 2026
1 adult · Economy · Round-trip totals
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| From | Destination | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| Miami (MIA) | Chicago (MDW) | Nov 7–14, 2026 · 7 days | Out: Southwest Airlines 2466 · Nonstop · 3h 10m · 15:00–17:10 local; Return: Southwest Airlines 2383 · Nonstop · 3h 0m · 07:40–11:40 local | $433 · Save $24 | $457 | Customer link — Open these flights in Axel · Optional: check axel prices |
| San Francisco (SFO) | Chicago (MDW) | Nov 10–17, 2026 · 7 days | Out: Frontier Airlines 2930 / 2882 · 1 stop (DFW) · 9h 35m · 23:47–11:22 (November 11, 2026) local; Return: Frontier Airlines 2999 / 3999 · 1 stop (DFW) · 12h 2m · 12:27–22:29 local | $193 · Save $11 | $204 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Atlanta (ATL) | Chicago (MDW) | Nov 10–17, 2026 · 7 days | Out: Frontier Airlines 2291 · Nonstop · 1h 59m · 22:48–23:47 local; Return: Frontier Airlines 2144 · Nonstop · 2h 11m · 18:42–21:53 local | $71 · Save $4 | $75 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Denver (DEN) | Chicago (MDW) | Nov 10–17, 2026 · 7 days | Out: Southwest Airlines 878 / 878 · 1 stop (CVG) · 4h 15m · 14:25–19:40 local; Return: Frontier Airlines 2999 / 4463 · 1 stop (DFW) · 10h 7m · 12:27–21:34 local | $149 · Save $8 | $157 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Denver (DEN) | Chicago (MDW) | Nov 10–17, 2026 · 7 days | Out: Southwest Airlines 878 / 878 · 1 stop (CVG) · 4h 15m · 14:25–19:40 local; Return: Southwest Airlines 120 · Nonstop · 2h 40m · 10:50–12:30 local | $160 · Save $9 | $169 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Dallas (DFW) | Chicago (MDW) | Nov 10–17, 2026 · 7 days | Out: Frontier Airlines 2882 · Nonstop · 2h 21m · 09:01–11:22 local; Return: Frontier Airlines 2999 · Nonstop · 2h 42m · 12:27–15:09 local | $95 · Save $5 | $100 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Dulles (IAD) | Chicago (MDW) | Nov 10–17, 2026 · 7 days | Out: Frontier Airlines 1081 / 2291 · 1 stop (ATL) · 6h 40m · 18:07–23:47 local; Return: Frontier Airlines 2292 / 4410 · 1 stop (ATL) · 10h 4m · 06:08–17:12 local | $132 · Save $7 | $139 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Houston (IAH) | Chicago (MDW) | Nov 10–17, 2026 · 7 days | Out: Frontier Airlines 1404 / 2779 · 1 stop (ATL) · 11h 47m · 06:00–17:47 local; Return: Delta Air Lines 4688 / 1718 · 1 stop (DTW) · 5h 12m · 13:31–18:43 local | $244 · Save $14 | $258 | Customer link — Open these flights in Axel · Optional: check axel prices |
| New York (JFK) | Chicago (MDW) | Nov 10–17, 2026 · 7 days | Out: Delta Air Lines 2286 / 1063 · 1 stop (ATL) · 5h 24m · 06:00–10:24 local; Return: Delta Air Lines 1063 / 2398 · 1 stop (ATL) · 5h 9m · 11:27–17:36 local | $279 · Save $16 | $295 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Los Angeles (LAX) | Chicago (MDW) | Nov 10–17, 2026 · 7 days | Out: Frontier Airlines 4964 / 2882 · 1 stop (DFW) · 9h 19m · 00:03–11:22 local; Return: Frontier Airlines 2999 / 3211 · 1 stop (DFW) · 12h 51m · 12:27–23:18 local | $185 · Save $11 | $196 | Customer link — Open these flights in Axel · Optional: check axel prices |
| London (LHR) | Chicago (MDW) | Nov 10–17, 2026 · 7 days | Out: KLM Royal Dutch Airlines 1002 / 135 / 4677 · 2 stops (AMS, DTW) · 15h 24m · 08:40–18:04 local; Return: Delta Air Lines 1063 / 104 · 1 stop (ATL) · 12h 58m · 11:27–06:25 (November 18, 2026) local | $935 · Save $54 | $989 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Minneapolis (MSP) | Chicago (MDW) | Nov 10–17, 2026 · 7 days | Out: Frontier Airlines 3046 / 2291 · 1 stop (ATL) · 8h 46m · 15:01–23:47 local; Return: Southwest Airlines 455 · Nonstop · 1h 30m · 11:40–13:10 local | $132 · Save $7 | $139 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Seattle (SEA) | Chicago (MDW) | Nov 10–17, 2026 · 7 days | Out: Southwest Airlines 4975 · Nonstop · 3h 50m · 00:15–06:05 local; Return: Southwest Airlines 1597 · Nonstop · 4h 40m · 10:10–12:50 local | $277 · Save $16 | $293 | Customer link — Open these flights in Axel · Optional: check axel prices |
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December 2026
1 adult · Economy · Round-trip totals
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| From | Destination | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| Minneapolis (MSP) | Chicago (MDW) | Dec 4–6, 2026 · 2 days | Out: Southwest Airlines 3292 · Nonstop · 1h 40m · 17:55–19:35 local; Return: Southwest Airlines 2378 · Nonstop · 1h 35m · 22:05–23:40 local | $130 · Save $7 | $137 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Atlanta (ATL) | Chicago (MDW) | Dec 8–15, 2026 · 7 days | Out: Frontier Airlines 2779 · Nonstop · 2h 6m · 10:27–11:33 local; Return: Frontier Airlines 2144 · Nonstop · 2h 13m · 12:28–15:41 local | $87 · Save $5 | $92 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Denver (DEN) | Chicago (MDW) | Dec 8–15, 2026 · 7 days | Out: Southwest Airlines 1697 · Nonstop · 2h 20m · 08:55–12:15 local; Return: Frontier Airlines 2144 / 3293 · 1 stop (ATL) · 8h 29m · 12:28–19:57 local | $147 · Save $8 | $155 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Denver (DEN) | Chicago (MDW) | Dec 8–15, 2026 · 7 days | Out: Southwest Airlines 1697 · Nonstop · 2h 20m · 08:55–12:15 local; Return: Southwest Airlines 3718 · Nonstop · 2h 45m · 20:55–22:40 local | $154 · Save $9 | $163 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Dallas (DFW) | Chicago (MDW) | Dec 8–15, 2026 · 7 days | Out: Delta Air Lines 893 / 2417 · 1 stop (ATL) · 4h 49m · 07:15–12:04 local; Return: Frontier Airlines 2144 / 3097 · 1 stop (ATL) · 8h 9m · 12:28–20:37 local | $160 · Save $9 | $169 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Dallas (DFW) | Chicago (MDW) | Dec 8–15, 2026 · 7 days | Out: Delta Air Lines 893 / 2417 · 1 stop (ATL) · 4h 49m · 07:15–12:04 local; Return: Delta Air Lines 1285 / 961 · 1 stop (ATL) · 5h 16m · 06:00–11:16 local | $196 · Save $11 | $207 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Houston (IAH) | Chicago (MDW) | Dec 8–15, 2026 · 7 days | Out: Delta Air Lines 1069 / 1063 · 1 stop (ATL) · 5h 3m · 05:25–10:28 local; Return: Delta Air Lines 4688 / 1718 · 1 stop (DTW) · 4h 58m · 13:41–18:39 local | $219 · Save $12 | $231 | Customer link — Open these flights in Axel · Optional: check axel prices |
| New York (JFK) | Chicago (MDW) | Dec 8–15, 2026 · 7 days | Out: Delta Air Lines 2286 / 1063 · 1 stop (ATL) · 5h 28m · 06:00–10:28 local; Return: Delta Air Lines 4714 / 2692 · 1 stop (MSP) · 5h 36m · 17:30–00:06 (December 16, 2026) local | $279 · Save $16 | $295 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Los Angeles (LAX) | Chicago (MDW) | Dec 8–15, 2026 · 7 days | Out: Southwest Airlines 2518 · Nonstop · 4h 0m · 23:55–05:55 (December 9, 2026) local; Return: Southwest Airlines 2953 · Nonstop · 4h 40m · 21:15–23:55 local | $152 · Save $9 | $161 | Customer link — Open these flights in Axel · Optional: check axel prices |
| London (LHR) | Chicago (MDW) | Dec 8–15, 2026 · 7 days | Out: KLM Royal Dutch Airlines 1002 / 135 / 4677 · 2 stops (AMS, DTW) · 15h 21m · 08:40–18:01 local; Return: Delta Air Lines 4901 / 160 / 1003 · 2 stops (MSP, AMS) · 14h 21m · 12:39–09:00 (December 16, 2026) local | $872 · Save $50 | $922 | Customer link — Open these flights in Axel · Optional: check axel prices |
| London (LHR) | Chicago (MDW) | Dec 8–15, 2026 · 7 days | Out: KLM Royal Dutch Airlines 1002 / 135 / 4677 · 2 stops (AMS, DTW) · 15h 21m · 08:40–18:01 local; Return: Delta Air Lines 2417 / 104 · 1 stop (ATL) · 11h 23m · 13:02–06:25 (December 16, 2026) local | $935 · Save $54 | $989 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Miami (MIA) | Chicago (MDW) | Dec 8–15, 2026 · 7 days | Out: Frontier Airlines 2483 / 2779 · 1 stop (ATL) · 5h 28m · 07:05–11:33 local; Return: Southwest Airlines 1362 · Nonstop · 3h 0m · 13:25–17:25 local | $213 · Save $12 | $225 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Seattle (SEA) | Chicago (MDW) | Dec 8–15, 2026 · 7 days | Out: Southwest Airlines 1550 · Nonstop · 3h 55m · 06:30–12:25 local; Return: Southwest Airlines 1597 · Nonstop · 4h 40m · 10:10–12:50 local | $277 · Save $16 | $293 | Customer link — Open these flights in Axel · Optional: check axel prices |
| San Francisco (SFO) | Chicago (MDW) | Dec 8–15, 2026 · 7 days | Out: Southwest Airlines 2331 · Nonstop · 4h 15m · 06:00–12:15 local; Return: Southwest Airlines 1536 · Nonstop · 4h 50m · 21:05–23:55 local | $231 · Save $12 | $243 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Dulles (IAD) | Chicago (MDW) | Dec 22–29, 2026 · 7 days | Out: Frontier Airlines 4355 / 1457 · 1 stop (MCO) · 22h 24m · 22:06–19:30 (December 23, 2026) local; Return: Delta Air Lines 4690 / 4704 · 1 stop (DTW) · 3h 55m · 18:15–23:10 local | $212 · Save $11 | $223 | Customer link — Open these flights in Axel · Optional: check axel prices |
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January 2027
1 adult · Economy · Round-trip totals
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| From | Destination | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| New York (JFK) | Chicago (MDW) | Jan 12–19, 2027 · 7 days | Out: Delta Air Lines 2293 / 1076 · 1 stop (ATL) · 6h 2m · 17:15–22:17 local; Return: Delta Air Lines 1063 / 2398 · 1 stop (ATL) · 5h 58m · 10:51–17:49 local | $319 · Save $18 | $337 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Los Angeles (LAX) | Chicago (MDW) | Jan 12–19, 2027 · 7 days | Out: Southwest Airlines 2264 · Nonstop · 4h 0m · 06:35–12:35 local; Return: Southwest Airlines 2681 · Nonstop · 4h 30m · 19:35–22:05 local | $224 · Save $13 | $237 | Customer link — Open these flights in Axel · Optional: check axel prices |
| London (LHR) | Chicago (MDW) | Jan 12–19, 2027 · 7 days | Out: KLM Royal Dutch Airlines 1004 / 75 / 1076 · 2 stops (AMS, ATL) · 18h 17m · 10:00–22:17 local; Return: Delta Air Lines 1728 / 36 · 1 stop (ATL) · 11h 55m · 17:45–11:40 (January 20, 2027) local | $861 · Save $50 | $911 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Miami (MIA) | Chicago (MDW) | Jan 12–19, 2027 · 7 days | Out: Southwest Airlines 1968 · Nonstop · 3h 25m · 12:30–14:55 local; Return: Frontier Airlines 2144 / 2484 · 1 stop (ATL) · 6h 18m · 13:18–20:36 local | $255 · Save $14 | $269 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Miami (MIA) | Chicago (MDW) | Jan 12–19, 2027 · 7 days | Out: Southwest Airlines 1968 · Nonstop · 3h 25m · 12:30–14:55 local; Return: Southwest Airlines 1092 · Nonstop · 3h 0m · 17:45–21:45 local | $319 · Save $18 | $337 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Minneapolis (MSP) | Chicago (MDW) | Jan 12–19, 2027 · 7 days | Out: Southwest Airlines 607 · Nonstop · 1h 30m · 14:55–16:25 local; Return: Southwest Airlines 2711 · Nonstop · 1h 30m · 13:15–14:45 local | $111 · Save $6 | $117 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Seattle (SEA) | Chicago (MDW) | Jan 12–19, 2027 · 7 days | Out: Southwest Airlines 3490 · Nonstop · 3h 55m · 06:20–12:15 local; Return: Southwest Airlines 3958 · Nonstop · 4h 45m · 19:55–22:40 local | $311 · Save $18 | $329 | Customer link — Open these flights in Axel · Optional: check axel prices |
| San Francisco (SFO) | Chicago (MDW) | Jan 12–19, 2027 · 7 days | Out: Southwest Airlines 3995 · Nonstop · 4h 5m · 06:20–12:25 local; Return: Southwest Airlines 3960 · Nonstop · 4h 50m · 19:50–22:40 local | $282 · Save $15 | $297 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Atlanta (ATL) | Chicago (MDW) | Jan 12–19, 2027 · 7 days | Out: Frontier Airlines 2291 · Nonstop · 2h 2m · 22:44–23:46 local; Return: Frontier Airlines 2144 · Nonstop · 2h 7m · 13:18–16:25 local | $121 · Save $7 | $128 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Denver (DEN) | Chicago (MDW) | Jan 12–19, 2027 · 7 days | Out: Frontier Airlines 3294 / 2291 · 1 stop (ATL) · 11h 35m · 11:11–23:46 local; Return: Frontier Airlines 2144 / 3599 · 1 stop (ATL) · 9h 7m · 13:18–21:25 local | $209 · Save $11 | $220 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Dallas (DFW) | Chicago (MDW) | Jan 12–19, 2027 · 7 days | Out: Frontier Airlines 2496 / 2291 · 1 stop (ATL) · 6h 56m · 16:50–23:46 local; Return: Frontier Airlines 2144 / 1269 · 1 stop (ATL) · 9h 43m · 13:18–23:01 local | $152 · Save $8 | $160 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Dallas (DFW) | Chicago (MDW) | Jan 12–19, 2027 · 7 days | Out: Frontier Airlines 2496 / 2291 · 1 stop (ATL) · 6h 56m · 16:50–23:46 local; Return: Frontier Airlines 2144 / 3097 · 1 stop (ATL) · 6h 12m · 13:18–19:30 local | $188 · Save $10 | $198 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Dulles (IAD) | Chicago (MDW) | Jan 12–19, 2027 · 7 days | Out: Delta Air Lines 5511 / 4834 · 1 stop (DTW) · 4h 15m · 06:01–09:16 local; Return: Frontier Airlines 2144 / 3692 · 1 stop (ATL) · 10h 1m · 13:18–00:19 (January 20, 2027) local | $236 · Save $13 | $249 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Dulles (IAD) | Chicago (MDW) | Jan 12–19, 2027 · 7 days | Out: Delta Air Lines 5511 / 4834 · 1 stop (DTW) · 4h 15m · 06:01–09:16 local; Return: Delta Air Lines 4677 / 4704 · 1 stop (DTW) · 3h 37m · 18:40–23:17 local | $319 · Save $18 | $337 | Customer link — Open these flights in Axel · Optional: check axel prices |
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March 2027
5 adults · Economy · Round-trip totals
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| From | Destination | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| Atlanta (ATL) | Chicago (MDW) | Mar 22–26, 2027 · 4 days | Out: Frontier Airlines 2291 · Nonstop · 2h 2m · 22:44–23:46 local; Return: Frontier Airlines 2144 · Nonstop · 2h 7m · 13:18–16:25 local | $1,506 · Save $84 | $1,590 | Customer link — Open these flights in Axel · Optional: check axel prices |
1 adult · Economy · Round-trip totals
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| From | Destination | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| Seattle (SEA) | Chicago (MDW) | Mar 9–14, 2027 · 5 days | Out: Southwest Airlines 3490 · Nonstop · 3h 50m · 06:35–12:25 local; Return: Southwest Airlines 2972 · Nonstop · 4h 45m · 10:05–12:50 local | $430 · Save $23 | $453 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Dallas (DFW) | Chicago (MDW) | Mar 15–18, 2027 · 3 days | Out: Frontier Airlines 2882 · Nonstop · 2h 22m · 09:51–12:13 local; Return: Frontier Airlines 2144 / 3097 · 1 stop (ATL) · 6h 12m · 13:18–19:30 local | $346 · Save $18 | $364 | Customer link — Open these flights in Axel · Optional: check axel prices |
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- This page: Flights to Chicago (MDW): deals from 12 cities. Flights to Chicago (MDW) from Seattle, New York, San Francisco Bay Area, Los Angeles, Miami or Fort Lauderdale, Denver, Minneapolis, Houston, Washington, DC, Dallas-Fort Worth, London, Atlanta. Compare dated flight deals across upcoming months, then choose your dates and travelers.
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