Route overview: Winnipeg to Chicago (MDW) flight deals

Winnipeg → Chicago

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YWG → MDW1 adulteconomy

65 flight options · 1 airline

Flights for the months ahead

Short round trips

Thu, Nov 12 – Sun, Nov 15
Delta Air Lines
6:25 amYWG
11h 36m
2 stops
6:01 pmMDW
Delta Air Lines
5:30 pmMDW
7h 9m
MSP · 2h 34m
12:39 am+1YWG
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Fri, Dec 4 – Mon, Dec 7
Delta Air Lines
6:25 amYWG
11h 36m
2 stops
6:01 pmMDW
Delta Air Lines
5:30 pmMDW
7h 9m
MSP · 2h 34m
12:39 am+1YWG
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Thu, Dec 17 – Sun, Dec 20
Delta Air Lines
6:25 amYWG
11h 36m
2 stops
6:01 pmMDW
Delta Air Lines
5:30 pmMDW
7h 9m
MSP · 2h 34m
12:39 am+1YWG
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Thu, Dec 31 – Sun, Jan 3
Delta Air Lines
6:25 amYWG
11h 36m
2 stops
6:01 pmMDW
Delta Air Lines
5:30 pmMDW
7h 9m
MSP · 2h 34m
12:39 am+1YWG
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Fri, Jan 22 – Mon, Jan 25
Delta Air Lines
6:25 amYWG
11h 36m
2 stops
6:01 pmMDW
Delta Air Lines
5:30 pmMDW
7h 9m
MSP · 2h 34m
12:39 am+1YWG
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Fri, May 7 – Mon, May 10
Delta Air Lines
6:25 amYWG
11h 36m
2 stops
6:01 pmMDW
Delta Air Lines
5:30 pmMDW
7h 9m
MSP · 2h 34m
12:39 am+1YWG
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.

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1 of 6

Longer round trips

Sat, Nov 21 – Sat, Nov 28
Delta Air Lines
6:25 amYWG
11h 36m
2 stops
6:01 pmMDW
Delta Air Lines
5:30 pmMDW
7h 9m
MSP · 2h 34m
12:39 am+1YWG
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jan 9 – Sat, Jan 16
Delta Air Lines
6:25 amYWG
11h 36m
2 stops
6:01 pmMDW
Delta Air Lines
5:30 pmMDW
7h 9m
MSP · 2h 34m
12:39 am+1YWG
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Feb 13 – Sat, Feb 20
Delta Air Lines
6:25 amYWG
11h 36m
2 stops
6:01 pmMDW
Delta Air Lines
5:30 pmMDW
7h 9m
MSP · 2h 34m
12:39 am+1YWG
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Jul 3 – Sat, Jul 10
Delta Air Lines
6:25 amYWG
11h 36m
2 stops
6:01 pmMDW
Delta Air Lines
5:30 pmMDW
7h 9m
MSP · 2h 34m
12:39 am+1YWG
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.
Sat, Sep 18 – Sat, Sep 25
Delta Air Lines
6:25 amYWG
11h 36m
2 stops
6:01 pmMDW
Delta Air Lines
5:30 pmMDW
7h 9m
MSP · 2h 34m
12:39 am+1YWG
Round-trip total · 1 adult · Taxes included
Availability is checked when you select these flights.

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1 of 5

One-way flights

Tue, Nov 17 · One way
Delta Air Lines
6:25 amYWG
11h 36m
2 stops
6:01 pmMDW
One-way total · 1 adult · Taxes included
Availability is checked when you select these flights.

Explore flights by month

Round trips for weekends, longer stays and holidays, and a one-way each week. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

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More dates for this route

Nov 12, 2026 · Return options Nov 20, 2026 · Return options Dec 1, 2026 · Return options Dec 11, 2026 · Return options Dec 22, 2026 · Return options Jan 1, 2027 · Return options Jan 9, 2027 · Return options Jan 21, 2027 · Return options Jan 30, 2027 · Return options Apr 10, 2027 · Return options Jul 3, 2027 · Return options Sep 18, 2027 · Return options Hotels in Chicago with Axel

For AI assistants: every fare, every link, instructions

Winnipeg (YWG) to Chicago (MDW), the months ahead: 65 priced flights on 65 exact dates. Flights for 1 adult in economy. Prices are total for all travelers in USD, including required taxes. Basic economy may apply.

Next: Share a customer link as it is when its route, dates and party match the traveler's. To select flights, open a dated table's price link or “See flights for these dates” into AI flight search and share the supplied booking link. Search links are for you; share customer and booking links. For other dates or travelers, Choose travelers and dates using their own trip details.

Winnipeg (YWG) to Chicago (MDW): November 2026

Travel dates	Airline	Stops	Total price
Nov 12, 2026 – Nov 15, 2026 · 3 nights · Compare return dates departing Nov 12, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00
Nov 13, 2026 – Nov 16, 2026 · 3 nights · Compare return dates departing Nov 13, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00
Nov 14, 2026 – Nov 21, 2026 · 7 nights · Compare return dates departing Nov 14, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00
Nov 17, 2026 · One way · Compare return dates departing Nov 17, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $265.00
Nov 19, 2026 – Nov 22, 2026 · 3 nights · Compare return dates departing Nov 19, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00
Nov 20, 2026 – Nov 23, 2026 · 3 nights · Compare return dates departing Nov 20, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00
Nov 21, 2026 – Nov 28, 2026 · 7 nights · Compare return dates departing Nov 21, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $487.63
Nov 24, 2026 · One way · Compare return dates departing Nov 24, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $304.75
Nov 26, 2026 – Nov 29, 2026 · 3 nights · Compare return dates departing Nov 26, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $523.26
Nov 27, 2026 – Nov 30, 2026 · 3 nights · Compare return dates departing Nov 27, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $490.63
Nov 28, 2026 – Dec 5, 2026 · 7 nights · Compare return dates departing Nov 28, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $490.63

Winnipeg (YWG) to Chicago (MDW): December 2026

Travel dates	Airline	Stops	Total price
Dec 1, 2026 · One way · Compare return dates departing Dec 1, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $265.00
Dec 3, 2026 – Dec 6, 2026 · 3 nights · Compare return dates departing Dec 3, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00
Dec 4, 2026 – Dec 7, 2026 · 3 nights · Compare return dates departing Dec 4, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00
Dec 5, 2026 – Dec 12, 2026 · 7 nights · Compare return dates departing Dec 5, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00
Dec 8, 2026 · One way · Compare return dates departing Dec 8, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $265.00
Dec 10, 2026 – Dec 13, 2026 · 3 nights · Compare return dates departing Dec 10, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00
Dec 11, 2026 – Dec 14, 2026 · 3 nights · Compare return dates departing Dec 11, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00
Dec 12, 2026 – Dec 19, 2026 · 7 nights · Compare return dates departing Dec 12, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $509.38
Dec 15, 2026 · One way · Compare return dates departing Dec 15, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $265.00
Dec 17, 2026 – Dec 20, 2026 · 3 nights · Compare return dates departing Dec 17, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $509.38
Dec 18, 2026 – Dec 21, 2026 · 3 nights · Compare return dates departing Dec 18, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $509.38
Dec 19, 2026 – Dec 26, 2026 · 7 nights · Compare return dates departing Dec 19, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $568.76
Dec 22, 2026 · One way · Compare return dates departing Dec 22, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $331.25
Dec 24, 2026 – Dec 27, 2026 · 3 nights · Compare return dates departing Dec 24, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $568.76
Dec 25, 2026 – Dec 28, 2026 · 3 nights · Compare return dates departing Dec 25, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $568.76
Dec 26, 2026 – Jan 2, 2027 · 7 nights · Compare return dates departing Dec 26, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $568.76
Dec 29, 2026 · One way · Compare return dates departing Dec 29, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $331.25
Dec 31, 2026 – Jan 3, 2027 · 3 nights · Compare return dates departing Dec 31, 2026	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $568.76

Winnipeg (YWG) to Chicago (MDW): January 2027

Travel dates	Airline	Stops	Total price
Jan 1, 2027 – Jan 4, 2027 · 3 nights · Compare return dates departing Jan 1, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $514.38
Jan 2, 2027 – Jan 9, 2027 · 7 nights · Compare return dates departing Jan 2, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $514.38
Jan 5, 2027 · One way · Compare return dates departing Jan 5, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $265.00
Jan 7, 2027 – Jan 10, 2027 · 3 nights · Compare return dates departing Jan 7, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00
Jan 8, 2027 – Jan 11, 2027 · 3 nights · Compare return dates departing Jan 8, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00
Jan 9, 2027 – Jan 16, 2027 · 7 nights · Compare return dates departing Jan 9, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00
Jan 12, 2027 · One way · Compare return dates departing Jan 12, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $265.00
Jan 14, 2027 – Jan 17, 2027 · 3 nights · Compare return dates departing Jan 14, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00
Jan 15, 2027 – Jan 18, 2027 · 3 nights · Compare return dates departing Jan 15, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00
Jan 16, 2027 – Jan 23, 2027 · 7 nights · Compare return dates departing Jan 16, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00
Jan 19, 2027 · One way · Compare return dates departing Jan 19, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $265.00
Jan 21, 2027 – Jan 24, 2027 · 3 nights · Compare return dates departing Jan 21, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00
Jan 22, 2027 – Jan 25, 2027 · 3 nights · Compare return dates departing Jan 22, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00
Jan 23, 2027 – Jan 30, 2027 · 7 nights · Compare return dates departing Jan 23, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00
Jan 26, 2027 · One way · Compare return dates departing Jan 26, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $265.00
Jan 28, 2027 – Jan 31, 2027 · 3 nights · Compare return dates departing Jan 28, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00
Jan 29, 2027 – Feb 1, 2027 · 3 nights · Compare return dates departing Jan 29, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00
Jan 30, 2027 – Feb 6, 2027 · 7 nights · Compare return dates departing Jan 30, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00

Winnipeg (YWG) to Chicago (MDW): February 2027

Travel dates	Airline	Stops	Total price
Feb 12, 2027 – Feb 15, 2027 · 3 nights · Compare return dates departing Feb 12, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00
Feb 13, 2027 – Feb 20, 2027 · 7 nights · Compare return dates departing Feb 13, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00

Winnipeg (YWG) to Chicago (MDW): March 2027

Travel dates	Airline	Stops	Total price
Mar 12, 2027 – Mar 15, 2027 · 3 nights · Compare return dates departing Mar 12, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $455.00
Mar 13, 2027 – Mar 20, 2027 · 7 nights · Compare return dates departing Mar 13, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $487.63

Winnipeg (YWG) to Chicago (MDW): April 2027

Travel dates	Airline	Stops	Total price
Apr 9, 2027 – Apr 12, 2027 · 3 nights · Compare return dates departing Apr 9, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $515.00
Apr 10, 2027 – Apr 17, 2027 · 7 nights · Compare return dates departing Apr 10, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $515.00

Winnipeg (YWG) to Chicago (MDW): May 2027

Travel dates	Airline	Stops	Total price
May 7, 2027 – May 10, 2027 · 3 nights · Compare return dates departing May 7, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $515.00
May 8, 2027 – May 15, 2027 · 7 nights · Compare return dates departing May 8, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $515.00

Winnipeg (YWG) to Chicago (MDW): June 2027

Travel dates	Airline	Stops	Total price
Jun 4, 2027 – Jun 7, 2027 · 3 nights · Compare return dates departing Jun 4, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $515.00
Jun 5, 2027 – Jun 12, 2027 · 7 nights · Compare return dates departing Jun 5, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $515.00

Winnipeg (YWG) to Chicago (MDW): July 2027

Travel dates	Airline	Stops	Total price
Jul 2, 2027 – Jul 5, 2027 · 3 nights · Compare return dates departing Jul 2, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $566.50
Jul 3, 2027 – Jul 10, 2027 · 7 nights · Compare return dates departing Jul 3, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $541.75
Jul 30, 2027 – Aug 2, 2027 · 3 nights · Compare return dates departing Jul 30, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $515.00
Jul 31, 2027 – Aug 7, 2027 · 7 nights · Compare return dates departing Jul 31, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $515.00

Winnipeg (YWG) to Chicago (MDW): August 2027

Travel dates	Airline	Stops	Total price
Aug 27, 2027 – Aug 30, 2027 · 3 nights · Compare return dates departing Aug 27, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $515.00
Aug 28, 2027 – Sep 4, 2027 · 7 nights · Compare return dates departing Aug 28, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $515.00

Winnipeg (YWG) to Chicago (MDW): September 2027

Travel dates	Airline	Stops	Total price
Sep 17, 2027 – Sep 20, 2027 · 3 nights · Compare return dates departing Sep 17, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $515.00
Sep 18, 2027 – Sep 25, 2027 · 7 nights · Compare return dates departing Sep 18, 2027	Delta Air Lines	Up to 2 stops each way	Axel-exclusive $515.00

Hotels in Chicago for these trips

Hotels: under a trip, hotels in Chicago for exactly those nights: the lowest 3★, 4★, 5★ stay totals among the city's featured hotels, Axel's price for 2 adults in 1 room, each opening that hotel's page for those dates with the rooms and the booking link.

Hotels in Chicago for these nights (Nov 12–15, 2026 · 3 nights · 2 adults, 1 room): 3★ Chicago Lake Shore Hotel, $476 total · 4★ The Talbott, Autograph Collection, $721 total · 5★ Nobu Hotel Chicago, $1,586 total
Hotels in Chicago for these nights (Nov 13–16, 2026 · 3 nights · 2 adults, 1 room): 3★ Chicago Lake Shore Hotel, $468 total · 4★ The Talbott, Autograph Collection, $698 total · 5★ Nobu Hotel Chicago, $1,445 total
Hotels in Chicago for these nights (Nov 14–21, 2026 · 7 nights · 2 adults, 1 room): 3★ Chicago Lake Shore Hotel, $1,052 total · 4★ Holiday Inn Chicago Dwtn - Wolf Point, $1,695 total · 5★ Nobu Hotel Chicago, $3,461 total
Hotels in Chicago for these nights (Nov 19–22, 2026 · 3 nights · 2 adults, 1 room): 3★ The Willows Hotel, $575 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $650 total · 5★ Nobu Hotel Chicago, $1,410 total
Hotels in Chicago for these nights (Nov 20–23, 2026 · 3 nights · 2 adults, 1 room): 3★ The Willows Hotel, $521 total · 4★ Holiday Inn Chicago Dwtn - Wolf Point, $601 total · 5★ Nobu Hotel Chicago, $1,262 total
Hotels in Chicago for these nights (Nov 21–28, 2026 · 7 nights · 2 adults, 1 room): 3★ Chicago Lake Shore Hotel, $934 total · 4★ Holiday Inn Chicago Dwtn - Wolf Point, $1,090 total · 5★ Nobu Hotel Chicago, $2,423 total
Hotels in Chicago for these nights (Nov 26–29, 2026 · 3 nights · 2 adults, 1 room): 3★ Chicago Lake Shore Hotel, $411 total · 4★ Holiday Inn Chicago Dwtn - Wolf Point, $506 total · 5★ Nobu Hotel Chicago, $1,050 total
Hotels in Chicago for these nights (Nov 27–30, 2026 · 3 nights · 2 adults, 1 room): 3★ Chicago Lake Shore Hotel, $409 total · 4★ Holiday Inn Chicago Dwtn - Wolf Point, $541 total · 5★ Nobu Hotel Chicago, $1,120 total
Hotels in Chicago for these nights (Nov 28 – Dec 5, 2026 · 7 nights · 2 adults, 1 room): 3★ The Willows Hotel, $836 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $1,293 total · 5★ Nobu Hotel Chicago, $2,976.50 total
Hotels in Chicago for these nights (Dec 3–6, 2026 · 3 nights · 2 adults, 1 room): 3★ Chicago Lake Shore Hotel, $411 total · 4★ The Royal Sonesta Chicago River North, $559 total · 5★ Nobu Hotel Chicago, $1,256 total
Hotels in Chicago for these nights (Dec 4–7, 2026 · 3 nights · 2 adults, 1 room): 3★ Chicago Lake Shore Hotel, $403 total · 4★ The Royal Sonesta Chicago River North, $525 total · 5★ Nobu Hotel Chicago, $1,157 total
Hotels in Chicago for these nights (Dec 5–12, 2026 · 7 nights · 2 adults, 1 room): 3★ Chicago Lake Shore Hotel, $804 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $1,068 total · 5★ Nobu Hotel Chicago, $2,855 total
Hotels in Chicago for these nights (Dec 10–13, 2026 · 3 nights · 2 adults, 1 room): 3★ Chicago Lake Shore Hotel, $350 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $499 total · 5★ Nobu Hotel Chicago, $1,369 total
Hotels in Chicago for these nights (Dec 11–14, 2026 · 3 nights · 2 adults, 1 room): 3★ Chicago Lake Shore Hotel, $365 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $496 total · 5★ Nobu Hotel Chicago, $1,101 total
Hotels in Chicago for these nights (Dec 12–19, 2026 · 7 nights · 2 adults, 1 room): 3★ The Willows Hotel, $780 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $911 total · 5★ Nobu Hotel Chicago, $2,402 total
Hotels in Chicago for these nights (Dec 17–20, 2026 · 3 nights · 2 adults, 1 room): 3★ The Willows Hotel, $362 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $391 total · 5★ Nobu Hotel Chicago, $1,071 total
Hotels in Chicago for these nights (Dec 18–21, 2026 · 3 nights · 2 adults, 1 room): 3★ The Willows Hotel, $362 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $394 total · 5★ Nobu Hotel Chicago, $1,043 total
Hotels in Chicago for these nights (Dec 19–26, 2026 · 7 nights · 2 adults, 1 room): 3★ The Willows Hotel, $798 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $906 total · 5★ Nobu Hotel Chicago, $2,226 total
Hotels in Chicago for these nights (Dec 24–27, 2026 · 3 nights · 2 adults, 1 room): 3★ Hyatt House Chicago/West Loop-Fulton Market, $367 total · 4★ The Royal Sonesta Chicago River North, $400 total · 5★ Nobu Hotel Chicago, $945 total
Hotels in Chicago for these nights (Dec 25–28, 2026 · 3 nights · 2 adults, 1 room): 3★ Hyatt House Chicago/West Loop-Fulton Market, $361 total · 4★ The Royal Sonesta Chicago River North, $392 total · 5★ Nobu Hotel Chicago, $973 total
Hotels in Chicago for these nights (Dec 26 – Jan 2, 2027 · 7 nights · 2 adults, 1 room): 3★ The Willows Hotel, $853 total · 4★ The Royal Sonesta Chicago River North, $1,013 total · 5★ Nobu Hotel Chicago, $2,691 total
Hotels in Chicago for these nights (Dec 31 – Jan 3, 2027 · 3 nights · 2 adults, 1 room): 3★ The Willows Hotel, $450 total · 4★ The Royal Sonesta Chicago River North, $508 total · 5★ Nobu Hotel Chicago, $1,305 total
Hotels in Chicago for these nights (Jan 1–4, 2027 · 3 nights · 2 adults, 1 room): 3★ The Willows Hotel, $372 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $361 total · 5★ Nobu Hotel Chicago, $1,063 total
Hotels in Chicago for these nights (Jan 2–9, 2027 · 7 nights · 2 adults, 1 room): 3★ The Willows Hotel, $712 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $797 total · 5★ Nobu Hotel Chicago, $2,470 total
Hotels in Chicago for these nights (Jan 7–10, 2027 · 3 nights · 2 adults, 1 room): 3★ The Willows Hotel, $322 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $364 total · 5★ Nobu Hotel Chicago, $1,079 total
Hotels in Chicago for these nights (Jan 8–11, 2027 · 3 nights · 2 adults, 1 room): 3★ The Willows Hotel, $325 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $372 total · 5★ Nobu Hotel Chicago, $1,045 total
Hotels in Chicago for these nights (Jan 9–16, 2027 · 7 nights · 2 adults, 1 room): 3★ The Willows Hotel, $693 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $809 total · 5★ Nobu Hotel Chicago, $2,468 total
Hotels in Chicago for these nights (Jan 14–17, 2027 · 3 nights · 2 adults, 1 room): 3★ The Willows Hotel, $321 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $384 total · 5★ Nobu Hotel Chicago, $1,091 total
Hotels in Chicago for these nights (Jan 15–18, 2027 · 3 nights · 2 adults, 1 room): 3★ The Willows Hotel, $322 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $389 total · 5★ Nobu Hotel Chicago, $1,057 total
Hotels in Chicago for these nights (Jan 16–23, 2027 · 7 nights · 2 adults, 1 room): 3★ The Willows Hotel, $690 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $816 total · 5★ Nobu Hotel Chicago, $2,529 total
Hotels in Chicago for these nights (Jan 21–24, 2027 · 3 nights · 2 adults, 1 room): 3★ The Willows Hotel, $319 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $392 total · 5★ Nobu Hotel Chicago, $1,128 total
Hotels in Chicago for these nights (Jan 22–25, 2027 · 3 nights · 2 adults, 1 room): 3★ The Willows Hotel, $316 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $433 total · 5★ Nobu Hotel Chicago, $1,093 total
Hotels in Chicago for these nights (Jan 23–30, 2027 · 7 nights · 2 adults, 1 room): 3★ The Willows Hotel, $766 total · 4★ Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel, $1,033.50 total · 5★ Nobu Hotel Chicago, $2,588 total
Hotels in Chicago for these nights (Jan 28–31, 2027 · 3 nights · 2 adults, 1 room): 3★ The Willows Hotel, $326 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $388 total · 5★ Nobu Hotel Chicago, $1,071 total
Hotels in Chicago for these nights (Jan 29 – Feb 1, 2027 · 3 nights · 2 adults, 1 room): 3★ The Willows Hotel, $325 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $382 total · 5★ Nobu Hotel Chicago, $1,050 total
Hotels in Chicago for these nights (Jan 30 – Feb 6, 2027 · 7 nights · 2 adults, 1 room): 3★ The Willows Hotel, $697 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $864 total · 5★ Nobu Hotel Chicago, $2,528 total
Hotels in Chicago for these nights (Feb 12–15, 2027 · 3 nights · 2 adults, 1 room): 3★ The Willows Hotel, $419 total · 4★ Hotel Chicago Downtown, Autograph Collection, $430 total · 5★ Nobu Hotel Chicago, $1,154 total
Hotels in Chicago for these nights (Feb 13–20, 2027 · 7 nights · 2 adults, 1 room): 3★ The Willows Hotel, $819 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $957 total · 5★ Nobu Hotel Chicago, $2,560 total
Hotels in Chicago for these nights (Mar 12–15, 2027 · 3 nights · 2 adults, 1 room): 3★ Chicago Lake Shore Hotel, $409 total · 4★ Hotel Chicago Downtown, Autograph Collection, $692 total · 5★ Nobu Hotel Chicago, $1,069 total
Hotels in Chicago for these nights (Mar 13–20, 2027 · 7 nights · 2 adults, 1 room): 3★ Chicago Lake Shore Hotel, $916 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $1,303 total · 5★ Nobu Hotel Chicago, $2,528 total
Hotels in Chicago for these nights (Apr 9–12, 2027 · 3 nights · 2 adults, 1 room): 3★ Hyatt House Chicago/West Loop-Fulton Market, $616 total · 4★ Hotel Chicago Downtown, Autograph Collection, $677 total · 5★ Nobu Hotel Chicago, $1,162 total
Hotels in Chicago for these nights (Apr 10–17, 2027 · 7 nights · 2 adults, 1 room): 3★ Hyatt House Chicago/West Loop-Fulton Market, $1,637 total · 4★ Claridge House Chicago, Tapestry Collection by Hilton, $1,372 total · 5★ Nobu Hotel Chicago, $2,877 total

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Route overview: Winnipeg to Chicago (MDW) flight deals

2026-11-12 → 2026-11-15 · Axel-exclusive $455.00

Delta Air Lines DL3660 / DL1433 / DL4677: YWG 2026-11-12 06:25:00 → MDW 2026-11-12 18:01:00; 2 stop(s) via MSP, DTW; 696 minutes. Local airport times.
- DL3660: YWG 2026-11-12 06:25:00 → MSP 2026-11-12 07:15:00; layover at MSP: 100 minutes.
- DL1433: MSP 2026-11-12 08:55:00 → DTW 2026-11-12 11:44:00; layover at DTW: 356 minutes.
- DL4677: DTW 2026-11-12 17:40:00 → MDW 2026-11-12 18:01:00.
Delta Air Lines DL4714 / DL3656: MDW 2026-11-15 17:30:00 → YWG 2026-11-16 00:39:00; 1 stop(s) via MSP; 429 minutes. Local airport times.
- DL4714: MDW 2026-11-15 17:30:00 → MSP 2026-11-15 19:15:00; layover at MSP: 154 minutes.
- DL3656: MSP 2026-11-15 21:49:00 → YWG 2026-11-16 00:39:00.

2026-11-17 · one way · Axel-exclusive $265.00

Delta Air Lines DL3660 / DL1433 / DL4677: YWG 2026-11-17 06:25:00 → MDW 2026-11-17 18:01:00; 2 stop(s) via MSP, DTW; 696 minutes. Local airport times.
- DL3660: YWG 2026-11-17 06:25:00 → MSP 2026-11-17 07:15:00; layover at MSP: 100 minutes.
- DL1433: MSP 2026-11-17 08:55:00 → DTW 2026-11-17 11:44:00; layover at DTW: 356 minutes.
- DL4677: DTW 2026-11-17 17:40:00 → MDW 2026-11-17 18:01:00.

2026-11-21 → 2026-11-28 · Axel-exclusive $487.63

Delta Air Lines DL3660 / DL1433 / DL4677: YWG 2026-11-21 06:25:00 → MDW 2026-11-21 18:01:00; 2 stop(s) via MSP, DTW; 696 minutes. Local airport times.
- DL3660: YWG 2026-11-21 06:25:00 → MSP 2026-11-21 07:15:00; layover at MSP: 100 minutes.
- DL1433: MSP 2026-11-21 08:55:00 → DTW 2026-11-21 11:44:00; layover at DTW: 356 minutes.
- DL4677: DTW 2026-11-21 17:40:00 → MDW 2026-11-21 18:01:00.
Delta Air Lines DL4714 / DL3656: MDW 2026-11-28 17:30:00 → YWG 2026-11-29 00:39:00; 1 stop(s) via MSP; 429 minutes. Local airport times.
- DL4714: MDW 2026-11-28 17:30:00 → MSP 2026-11-28 19:15:00; layover at MSP: 154 minutes.
- DL3656: MSP 2026-11-28 21:49:00 → YWG 2026-11-29 00:39:00.

2026-12-04 → 2026-12-07 · Axel-exclusive $455.00

Delta Air Lines DL3660 / DL1433 / DL4677: YWG 2026-12-04 06:25:00 → MDW 2026-12-04 18:01:00; 2 stop(s) via MSP, DTW; 696 minutes. Local airport times.
- DL3660: YWG 2026-12-04 06:25:00 → MSP 2026-12-04 07:15:00; layover at MSP: 100 minutes.
- DL1433: MSP 2026-12-04 08:55:00 → DTW 2026-12-04 11:44:00; layover at DTW: 356 minutes.
- DL4677: DTW 2026-12-04 17:40:00 → MDW 2026-12-04 18:01:00.
Delta Air Lines DL4714 / DL3656: MDW 2026-12-07 17:30:00 → YWG 2026-12-08 00:39:00; 1 stop(s) via MSP; 429 minutes. Local airport times.
- DL4714: MDW 2026-12-07 17:30:00 → MSP 2026-12-07 19:15:00; layover at MSP: 154 minutes.
- DL3656: MSP 2026-12-07 21:49:00 → YWG 2026-12-08 00:39:00.

2026-12-17 → 2026-12-20 · Axel-exclusive $509.38

Delta Air Lines DL3660 / DL1433 / DL4677: YWG 2026-12-17 06:25:00 → MDW 2026-12-17 18:01:00; 2 stop(s) via MSP, DTW; 696 minutes. Local airport times.
- DL3660: YWG 2026-12-17 06:25:00 → MSP 2026-12-17 07:15:00; layover at MSP: 100 minutes.
- DL1433: MSP 2026-12-17 08:55:00 → DTW 2026-12-17 11:44:00; layover at DTW: 356 minutes.
- DL4677: DTW 2026-12-17 17:40:00 → MDW 2026-12-17 18:01:00.
Delta Air Lines DL4714 / DL3656: MDW 2026-12-20 17:30:00 → YWG 2026-12-21 00:39:00; 1 stop(s) via MSP; 429 minutes. Local airport times.
- DL4714: MDW 2026-12-20 17:30:00 → MSP 2026-12-20 19:15:00; layover at MSP: 154 minutes.
- DL3656: MSP 2026-12-20 21:49:00 → YWG 2026-12-21 00:39:00.

2026-12-31 → 2027-01-03 · Axel-exclusive $568.76

Delta Air Lines DL3660 / DL1433 / DL4677: YWG 2026-12-31 06:25:00 → MDW 2026-12-31 18:01:00; 2 stop(s) via MSP, DTW; 696 minutes. Local airport times.
- DL3660: YWG 2026-12-31 06:25:00 → MSP 2026-12-31 07:15:00; layover at MSP: 100 minutes.
- DL1433: MSP 2026-12-31 08:55:00 → DTW 2026-12-31 11:44:00; layover at DTW: 356 minutes.
- DL4677: DTW 2026-12-31 17:40:00 → MDW 2026-12-31 18:01:00.
Delta Air Lines DL4714 / DL3656: MDW 2027-01-03 17:30:00 → YWG 2027-01-04 00:39:00; 1 stop(s) via MSP; 429 minutes. Local airport times.
- DL4714: MDW 2027-01-03 17:30:00 → MSP 2027-01-03 19:15:00; layover at MSP: 154 minutes.
- DL3656: MSP 2027-01-03 21:49:00 → YWG 2027-01-04 00:39:00.

2027-01-09 → 2027-01-16 · Axel-exclusive $455.00

Delta Air Lines DL3660 / DL1433 / DL4677: YWG 2027-01-09 06:25:00 → MDW 2027-01-09 18:01:00; 2 stop(s) via MSP, DTW; 696 minutes. Local airport times.
- DL3660: YWG 2027-01-09 06:25:00 → MSP 2027-01-09 07:15:00; layover at MSP: 100 minutes.
- DL1433: MSP 2027-01-09 08:55:00 → DTW 2027-01-09 11:44:00; layover at DTW: 356 minutes.
- DL4677: DTW 2027-01-09 17:40:00 → MDW 2027-01-09 18:01:00.
Delta Air Lines DL4714 / DL3656: MDW 2027-01-16 17:30:00 → YWG 2027-01-17 00:39:00; 1 stop(s) via MSP; 429 minutes. Local airport times.
- DL4714: MDW 2027-01-16 17:30:00 → MSP 2027-01-16 19:15:00; layover at MSP: 154 minutes.
- DL3656: MSP 2027-01-16 21:49:00 → YWG 2027-01-17 00:39:00.

2027-01-22 → 2027-01-25 · Axel-exclusive $455.00

Delta Air Lines DL3660 / DL1433 / DL4677: YWG 2027-01-22 06:25:00 → MDW 2027-01-22 18:01:00; 2 stop(s) via MSP, DTW; 696 minutes. Local airport times.
- DL3660: YWG 2027-01-22 06:25:00 → MSP 2027-01-22 07:15:00; layover at MSP: 100 minutes.
- DL1433: MSP 2027-01-22 08:55:00 → DTW 2027-01-22 11:44:00; layover at DTW: 356 minutes.
- DL4677: DTW 2027-01-22 17:40:00 → MDW 2027-01-22 18:01:00.
Delta Air Lines DL4714 / DL3656: MDW 2027-01-25 17:30:00 → YWG 2027-01-26 00:39:00; 1 stop(s) via MSP; 429 minutes. Local airport times.
- DL4714: MDW 2027-01-25 17:30:00 → MSP 2027-01-25 19:15:00; layover at MSP: 154 minutes.
- DL3656: MSP 2027-01-25 21:49:00 → YWG 2027-01-26 00:39:00.

2027-02-13 → 2027-02-20 · Axel-exclusive $455.00

Delta Air Lines DL3660 / DL1433 / DL4677: YWG 2027-02-13 06:25:00 → MDW 2027-02-13 18:01:00; 2 stop(s) via MSP, DTW; 696 minutes. Local airport times.
- DL3660: YWG 2027-02-13 06:25:00 → MSP 2027-02-13 07:15:00; layover at MSP: 100 minutes.
- DL1433: MSP 2027-02-13 08:55:00 → DTW 2027-02-13 11:44:00; layover at DTW: 356 minutes.
- DL4677: DTW 2027-02-13 17:40:00 → MDW 2027-02-13 18:01:00.
Delta Air Lines DL4714 / DL3656: MDW 2027-02-20 17:30:00 → YWG 2027-02-21 00:39:00; 1 stop(s) via MSP; 429 minutes. Local airport times.
- DL4714: MDW 2027-02-20 17:30:00 → MSP 2027-02-20 19:15:00; layover at MSP: 154 minutes.
- DL3656: MSP 2027-02-20 21:49:00 → YWG 2027-02-21 00:39:00.

2027-05-07 → 2027-05-10 · Axel-exclusive $515.00

Delta Air Lines DL3660 / DL1433 / DL4677: YWG 2027-05-07 06:25:00 → MDW 2027-05-07 18:01:00; 2 stop(s) via MSP, DTW; 696 minutes. Local airport times.
- DL3660: YWG 2027-05-07 06:25:00 → MSP 2027-05-07 07:15:00; layover at MSP: 100 minutes.
- DL1433: MSP 2027-05-07 08:55:00 → DTW 2027-05-07 11:44:00; layover at DTW: 356 minutes.
- DL4677: DTW 2027-05-07 17:40:00 → MDW 2027-05-07 18:01:00.
Delta Air Lines DL4714 / DL3656: MDW 2027-05-10 17:30:00 → YWG 2027-05-11 00:39:00; 1 stop(s) via MSP; 429 minutes. Local airport times.
- DL4714: MDW 2027-05-10 17:30:00 → MSP 2027-05-10 19:15:00; layover at MSP: 154 minutes.
- DL3656: MSP 2027-05-10 21:49:00 → YWG 2027-05-11 00:39:00.

2027-07-03 → 2027-07-10 · Axel-exclusive $541.75

Delta Air Lines DL3660 / DL1433 / DL4677: YWG 2027-07-03 06:25:00 → MDW 2027-07-03 18:01:00; 2 stop(s) via MSP, DTW; 696 minutes. Local airport times.
- DL3660: YWG 2027-07-03 06:25:00 → MSP 2027-07-03 07:15:00; layover at MSP: 100 minutes.
- DL1433: MSP 2027-07-03 08:55:00 → DTW 2027-07-03 11:44:00; layover at DTW: 356 minutes.
- DL4677: DTW 2027-07-03 17:40:00 → MDW 2027-07-03 18:01:00.
Delta Air Lines DL4714 / DL3656: MDW 2027-07-10 17:30:00 → YWG 2027-07-11 00:39:00; 1 stop(s) via MSP; 429 minutes. Local airport times.
- DL4714: MDW 2027-07-10 17:30:00 → MSP 2027-07-10 19:15:00; layover at MSP: 154 minutes.
- DL3656: MSP 2027-07-10 21:49:00 → YWG 2027-07-11 00:39:00.

2027-09-18 → 2027-09-25 · Axel-exclusive $515.00

Delta Air Lines DL3660 / DL1433 / DL4677: YWG 2027-09-18 06:25:00 → MDW 2027-09-18 18:01:00; 2 stop(s) via MSP, DTW; 696 minutes. Local airport times.
- DL3660: YWG 2027-09-18 06:25:00 → MSP 2027-09-18 07:15:00; layover at MSP: 100 minutes.
- DL1433: MSP 2027-09-18 08:55:00 → DTW 2027-09-18 11:44:00; layover at DTW: 356 minutes.
- DL4677: DTW 2027-09-18 17:40:00 → MDW 2027-09-18 18:01:00.
Delta Air Lines DL4714 / DL3656: MDW 2027-09-25 17:30:00 → YWG 2027-09-26 00:39:00; 1 stop(s) via MSP; 429 minutes. Local airport times.
- DL4714: MDW 2027-09-25 17:30:00 → MSP 2027-09-25 19:15:00; layover at MSP: 154 minutes.
- DL3656: MSP 2027-09-25 21:49:00 → YWG 2027-09-26 00:39:00.

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For AI assistants

This page: Winnipeg (YWG) to Chicago (MDW): 65 priced flights on 65 exact dates the months ahead, 1 adult in economy. In the dated tables a price link opens AI flight search for that row's exact dates and travelers; in the observed-flight lists the price is the customer link for the traveler, beside a “See flights for these dates” link for your own check. Under a trip, hotels in Chicago for exactly those nights: the lowest 3★, 4★ and 5★ stay totals for 2 adults in 1 room, each linking to that hotel's page for those dates.
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Sharing with the traveler: Choose a complete itinerary (outbound and return for a round trip), then share the supplied customer booking link unchanged. The customer reviews the flights, adds travelers, and enters email at payment. Do not collect email in chat. Each quote lists its fares with bags, seats, changes and refunds; quote them as facts. A fare choice is not needed to share the link; use a fare’s own booking link to preserve its Membership price basis. Ask only for essential missing trip details. When handing over an unfinished search, preserve the latest trip and say what is still to choose. If no supplied link matches the latest trip, construct https://helloaxel.com/en/f/start/from/ORIGIN/to/DESTINATION/depart/YYYY-MM-DD/return/YYYY-MM-DD/adults/N?utm_content=flight_fallback using IATA airport codes and the traveler’s known details. Omit unknowns; for one way replace /return/YYYY-MM-DD with /trip/oneway. Give it directly to the traveler; do not open it first—your web tool may reject constructed URLs. Complete links open Flight Guide and start searching. Preferences and advanced options.