Flights to Chicago (MDW): deals from 12 cities
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Flights to Chicago (MDW) by departure city
- Seattle to Chicago (MDW)
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Fares observed October 22 – 28, 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 |
| 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 24–Dec 1, 2026 · 7 days | Out: Southwest Airlines 3827 · Nonstop · 3h 50m · 06:15–12:05 local; Return: Southwest Airlines 3032 · Nonstop · 4h 50m · 20:45–23:35 local | $378 · Save $21 | $399 | Customer link — Open these flights in Axel · Optional: check axel prices |
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1 adult · Economy · Round-trip starting totals
| From | Destination | Travel dates | Outbound flight | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| Dulles (IAD) | Chicago (MDW) | Nov 9–16, 2026 · 7 days | Out: Frontier Airlines 4707 / 2779 · 1 stop (ATL) · 11h 15m · 07:32–17:47 local | From $264 · Save $15 | From $279 | Check Axel prices |
| Dulles (IAD) | Chicago (MDW) | Nov 9–16, 2026 · 7 days | Out: Delta Air Lines 1444 / 1728 · 1 stop (ATL) · 4h 46m · 12:32–16:18 local | From $398 · Save $21 | From $419 | 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
1 adult · Economy · One-way totals
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| From | Destination | Travel dates | Outbound flight | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| San Francisco (SFO) | Chicago (MDW) | Mar 29, 2027 | Out: Southwest Airlines 3805 · Nonstop · 4h 5m · 23:55–06:00 (March 30, 2027) local | $220 · Save $12 | $232 | Customer link — Open these flights in Axel · Optional: check axel prices |
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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April 2027
3 adults · Economy · Round-trip totals
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| From | Destination | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| Atlanta (ATL) | Chicago (MDW) | Apr 3–6, 2027 · 3 days | Out: Delta Air Lines 2417 · Nonstop · 1h 56m · 14:30–15:26 local; Return: Delta Air Lines 2417 · Nonstop · 1h 56m · 13:05–16:01 local | $1,035 · Save $54 | $1,089 | 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 |
|---|---|---|---|---|---|---|
| Atlanta (ATL) | Chicago (MDW) | Apr 3–6, 2027 · 3 days | Out: Southwest Airlines 191 · Nonstop · 1h 55m · 13:55–14:50 local; Return: Southwest Airlines 1717 · Nonstop · 1h 55m · 17:10–20:05 local | $314 · Save $17 | $331 | Customer link — Open these flights in Axel · Optional: check axel prices |
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June 2027
4 adults · Economy · Round-trip totals
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| From | Destination | Travel dates | Flights (out / return) | Axel | Airline fare | Search |
|---|---|---|---|---|---|---|
| Atlanta (ATL) | Chicago (MDW) | Jun 11–16, 2027 · 5 days | Out: Southwest Airlines 282 · Nonstop · 1h 50m · 11:35–12:25 local; Return: Southwest Airlines 637 · Nonstop · 1h 50m · 09:15–12:05 local | $1,309 · Save $75 | $1,384 | Customer link — Open these flights in Axel · Optional: check axel prices |
| Atlanta (ATL) | Chicago (MDW) | Jun 16–21, 2027 · 5 days | Out: Southwest Airlines 4641 · Nonstop · 1h 55m · 08:05–09:00 local; Return: Southwest Airlines 2579 · Nonstop · 1h 50m · 12:50–15:40 local | $1,309 · Save $75 | $1,384 | Customer link — Open these flights in Axel · Optional: check axel prices |
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Hotels in Chicago with Axel
Axel books the hotel too, at private rates shown beside the public rate for the same stay. Hotels in Chicago has the best recent deals, and a flight booked with Axel can make the hotel cheaper through the bundle.
Where to stay: Where to stay in Chicago: the 10 best neighborhoods, ranked · Chicago hotels where a family of four can share one room
Hotels with an Axel review in Chicago: Claridge House Chicago, Tapestry Collection by Hilton · Freehand Chicago · Warwick Allerton - Chicago · The Chicago Hotel Collection - Wrigleyville · The Chicago Hotel Collection Magnificent Mile Hotel & Suites · All 154 reviewed hotels in Chicago
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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.
- Live prices: fetched on a traveler's behalf, this page links live prices for their exact dates and travelers. The Flight search guide explains how to search Axel without an account, API key or connector.