Cleveland (CLE) to Chicago (MDW), Dec 18–20, 2026, return Dec 25–27, 2026: from $298 round trip

Cleveland (CLE) to Chicago (MDW), Dec 18–20, 2026, return Dec 25–27, 2026: from $298 round trip on Axel, checked Oct 29, 2026. Lowest published fare: $298 round trip, Axel-exclusive, Southwest Airlines, nonstop, Dec 18–25, 2026, 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.

See flights for these dates: each price link opens AI flight search for that row's exact dates and travelers. Select the complete itinerary there.

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 (Dec 18–25, 2026 · 7 nights · 2 adults, 1 room): 3★ Hotel Versey, $700 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $233 total · 5★ Sofitel Chicago Magnificent Mile, $1,675 total
• Hotels in Chicago for these nights (Dec 18–26, 2026 · 8 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $824 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $343 total · 5★ Sofitel Chicago Magnificent Mile, $1,889 total
• Hotels in Chicago for these nights (Dec 18–27, 2026 · 9 nights · 2 adults, 1 room): 3★ The Whitehall Hotel, BW Premier Collection, $941 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $385 total · 5★ Sofitel Chicago Magnificent Mile, $2,098 total
• Hotels in Chicago for these nights (Dec 19–25, 2026 · 6 nights · 2 adults, 1 room): 3★ Hotel Versey, $581 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $164 total · 5★ Sofitel Chicago Magnificent Mile, $1,473 total
• Hotels in Chicago for these nights (Dec 19–26, 2026 · 7 nights · 2 adults, 1 room): 3★ Hotel Versey, $712 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $274 total · 5★ Sofitel Chicago Magnificent Mile, $1,687 total
• Hotels in Chicago for these nights (Dec 19–27, 2026 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $804 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $316 total · 5★ Sofitel Chicago Magnificent Mile, $1,896 total
• Hotels in Chicago for these nights (Dec 20–25, 2026 · 5 nights · 2 adults, 1 room): 3★ Hotel Versey, $462 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $95 total · 5★ Sofitel Chicago Magnificent Mile, $1,159 total
• Hotels in Chicago for these nights (Dec 20–26, 2026 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $583 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $205 total · 5★ Sofitel Chicago Magnificent Mile, $1,373 total
• Hotels in Chicago for these nights (Dec 20–27, 2026 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $674 total · 4★ The Chicago Hotel Collection Ambassador Gold Coast, $247 total · 5★ Sofitel Chicago Magnificent Mile, $1,582 total

All hotels in Chicago

Route overview: Cleveland to Chicago (MDW) flight deals

2026-12-18 → 2026-12-26 · Axel-exclusive $298.13

• Southwest Airlines WN1218: CLE 2026-12-18 08:45:00 → MDW 2026-12-18 09:10:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN1129: MDW 2026-12-26 08:25:00 → CLE 2026-12-26 10:40:00; nonstop; 75 minutes. Local airport times.

2026-12-18 → 2026-12-25 · Axel-exclusive $382.50

• Delta Air Lines DL5359 / DL4677: CLE 2026-12-18 14:05:00 → MDW 2026-12-18 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
  • DL5359: CLE 2026-12-18 14:05:00 → DTW 2026-12-18 15:10:00; layover at DTW: 150 minutes.
  • DL4677: DTW 2026-12-18 17:40:00 → MDW 2026-12-18 18:01:00.
• Delta Air Lines DL4688 / DL4954: MDW 2026-12-25 13:31:00 → CLE 2026-12-25 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
  • DL4688: MDW 2026-12-25 13:31:00 → DTW 2026-12-25 15:44:00; layover at DTW: 116 minutes.
  • DL4954: DTW 2026-12-25 17:40:00 → CLE 2026-12-25 18:40:00.

2026-12-18 → 2026-12-27 · Axel-exclusive $298.13

• Southwest Airlines WN1218: CLE 2026-12-18 08:45:00 → MDW 2026-12-18 09:10:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN4528: MDW 2026-12-27 20:40:00 → CLE 2026-12-27 22:55:00; nonstop; 75 minutes. Local airport times.

2026-12-19 → 2026-12-27 · Axel-exclusive $331.26

• Southwest Airlines WN1218: CLE 2026-12-19 08:45:00 → MDW 2026-12-19 09:10:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN4528: MDW 2026-12-27 20:40:00 → CLE 2026-12-27 22:55:00; nonstop; 75 minutes. Local airport times.

2026-12-20 → 2026-12-26 · Axel-exclusive $331.26

• Southwest Airlines WN1220: CLE 2026-12-20 19:10:00 → MDW 2026-12-20 19:35:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN1129: MDW 2026-12-26 08:25:00 → CLE 2026-12-26 10:40:00; nonstop; 75 minutes. Local airport times.

2026-12-20 → 2026-12-27 · Axel-exclusive $331.26

• Southwest Airlines WN1220: CLE 2026-12-20 19:10:00 → MDW 2026-12-20 19:35:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN4528: MDW 2026-12-27 20:40:00 → CLE 2026-12-27 22:55:00; nonstop; 75 minutes. Local airport times.

2026-12-19 → 2026-12-25 · Axel-exclusive $331.26

• Southwest Airlines WN1218: CLE 2026-12-19 08:45:00 → MDW 2026-12-19 09:10:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN1129: MDW 2026-12-25 08:25:00 → CLE 2026-12-25 10:40:00; nonstop; 75 minutes. Local airport times.

2026-12-20 → 2026-12-25 · Axel-exclusive $331.26

• Southwest Airlines WN1218: CLE 2026-12-20 08:45:00 → MDW 2026-12-20 09:10:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN1129: MDW 2026-12-25 08:25:00 → CLE 2026-12-25 10:40:00; nonstop; 75 minutes. Local airport times.

2026-12-19 → 2026-12-26 · Axel-exclusive $331.26

• Southwest Airlines WN1220: CLE 2026-12-19 19:10:00 → MDW 2026-12-19 19:35:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN1129: MDW 2026-12-26 08:25:00 → CLE 2026-12-26 10:40:00; nonstop; 75 minutes. Local airport times.

2026-12-18 → 2026-12-27 · Axel-exclusive $298.13

• Southwest Airlines WN1220: CLE 2026-12-18 19:10:00 → MDW 2026-12-18 19:35:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN4528: MDW 2026-12-27 20:40:00 → CLE 2026-12-27 22:55:00; nonstop; 75 minutes. Local airport times.

2026-12-18 → 2026-12-25 · Axel-exclusive $298.13

• Southwest Airlines WN1218: CLE 2026-12-18 08:45:00 → MDW 2026-12-18 09:10:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN1129: MDW 2026-12-25 08:25:00 → CLE 2026-12-25 10:40:00; nonstop; 75 minutes. Local airport times.

2026-12-18 → 2026-12-25 · Axel-exclusive $298.13

• Southwest Airlines WN1220: CLE 2026-12-18 19:10:00 → MDW 2026-12-18 19:35:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN1129: MDW 2026-12-25 08:25:00 → CLE 2026-12-25 10:40:00; nonstop; 75 minutes. Local airport times.

2026-12-18 → 2026-12-26 · Axel-exclusive $298.13

• Southwest Airlines WN1220: CLE 2026-12-18 19:10:00 → MDW 2026-12-18 19:35:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN1129: MDW 2026-12-26 08:25:00 → CLE 2026-12-26 10:40:00; nonstop; 75 minutes. Local airport times.

2026-12-19 → 2026-12-27 · Axel-exclusive $331.26

• Southwest Airlines WN1220: CLE 2026-12-19 19:10:00 → MDW 2026-12-19 19:35:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN4528: MDW 2026-12-27 20:40:00 → CLE 2026-12-27 22:55:00; nonstop; 75 minutes. Local airport times.

2026-12-20 → 2026-12-26 · Axel-exclusive $331.26

• Southwest Airlines WN1218: CLE 2026-12-20 08:45:00 → MDW 2026-12-20 09:10:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN1129: MDW 2026-12-26 08:25:00 → CLE 2026-12-26 10:40:00; nonstop; 75 minutes. Local airport times.

2026-12-20 → 2026-12-27 · Axel-exclusive $331.26

• Southwest Airlines WN1218: CLE 2026-12-20 08:45:00 → MDW 2026-12-20 09:10:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN4528: MDW 2026-12-27 20:40:00 → CLE 2026-12-27 22:55:00; nonstop; 75 minutes. Local airport times.

2026-12-19 → 2026-12-25 · Axel-exclusive $331.26

• Southwest Airlines WN1220: CLE 2026-12-19 19:10:00 → MDW 2026-12-19 19:35:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN1129: MDW 2026-12-25 08:25:00 → CLE 2026-12-25 10:40:00; nonstop; 75 minutes. Local airport times.

2026-12-19 → 2026-12-26 · Axel-exclusive $331.26

• Southwest Airlines WN1218: CLE 2026-12-19 08:45:00 → MDW 2026-12-19 09:10:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN1129: MDW 2026-12-26 08:25:00 → CLE 2026-12-26 10:40:00; nonstop; 75 minutes. Local airport times.

2026-12-20 → 2026-12-25 · Axel-exclusive $331.26

• Southwest Airlines WN1220: CLE 2026-12-20 19:10:00 → MDW 2026-12-20 19:35:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN1129: MDW 2026-12-25 08:25:00 → CLE 2026-12-25 10:40:00; nonstop; 75 minutes. Local airport times.

2026-12-18 → 2026-12-27 · Axel-exclusive $382.50

• Delta Air Lines DL5359 / DL4677: CLE 2026-12-18 14:05:00 → MDW 2026-12-18 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
  • DL5359: CLE 2026-12-18 14:05:00 → DTW 2026-12-18 15:10:00; layover at DTW: 150 minutes.
  • DL4677: DTW 2026-12-18 17:40:00 → MDW 2026-12-18 18:01:00.
• Delta Air Lines DL4688 / DL4954: MDW 2026-12-27 13:31:00 → CLE 2026-12-27 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
  • DL4688: MDW 2026-12-27 13:31:00 → DTW 2026-12-27 15:44:00; layover at DTW: 116 minutes.
  • DL4954: DTW 2026-12-27 17:40:00 → CLE 2026-12-27 18:40:00.

2026-12-18 → 2026-12-26 · Axel-exclusive $382.50

• Delta Air Lines DL5359 / DL4677: CLE 2026-12-18 14:05:00 → MDW 2026-12-18 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
  • DL5359: CLE 2026-12-18 14:05:00 → DTW 2026-12-18 15:10:00; layover at DTW: 150 minutes.
  • DL4677: DTW 2026-12-18 17:40:00 → MDW 2026-12-18 18:01:00.
• Delta Air Lines DL4688 / DL4954: MDW 2026-12-26 13:31:00 → CLE 2026-12-26 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
  • DL4688: MDW 2026-12-26 13:31:00 → DTW 2026-12-26 15:44:00; layover at DTW: 116 minutes.
  • DL4954: DTW 2026-12-26 17:40:00 → CLE 2026-12-26 18:40:00.

2026-12-19 → 2026-12-27 · Axel-exclusive $425.00

• Delta Air Lines DL5359 / DL4677: CLE 2026-12-19 14:05:00 → MDW 2026-12-19 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
  • DL5359: CLE 2026-12-19 14:05:00 → DTW 2026-12-19 15:10:00; layover at DTW: 150 minutes.
  • DL4677: DTW 2026-12-19 17:40:00 → MDW 2026-12-19 18:01:00.
• Delta Air Lines DL4688 / DL4954: MDW 2026-12-27 13:31:00 → CLE 2026-12-27 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
  • DL4688: MDW 2026-12-27 13:31:00 → DTW 2026-12-27 15:44:00; layover at DTW: 116 minutes.
  • DL4954: DTW 2026-12-27 17:40:00 → CLE 2026-12-27 18:40:00.

2026-12-19 → 2026-12-25 · Axel-exclusive $425.00

• Delta Air Lines DL5359 / DL4677: CLE 2026-12-19 14:05:00 → MDW 2026-12-19 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
  • DL5359: CLE 2026-12-19 14:05:00 → DTW 2026-12-19 15:10:00; layover at DTW: 150 minutes.
  • DL4677: DTW 2026-12-19 17:40:00 → MDW 2026-12-19 18:01:00.
• Delta Air Lines DL4688 / DL4954: MDW 2026-12-25 13:31:00 → CLE 2026-12-25 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
  • DL4688: MDW 2026-12-25 13:31:00 → DTW 2026-12-25 15:44:00; layover at DTW: 116 minutes.
  • DL4954: DTW 2026-12-25 17:40:00 → CLE 2026-12-25 18:40:00.

2026-12-20 → 2026-12-26 · Axel-exclusive $425.00

• Delta Air Lines DL5359 / DL4677: CLE 2026-12-20 14:05:00 → MDW 2026-12-20 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
  • DL5359: CLE 2026-12-20 14:05:00 → DTW 2026-12-20 15:10:00; layover at DTW: 150 minutes.
  • DL4677: DTW 2026-12-20 17:40:00 → MDW 2026-12-20 18:01:00.
• Delta Air Lines DL4688 / DL4954: MDW 2026-12-26 13:31:00 → CLE 2026-12-26 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
  • DL4688: MDW 2026-12-26 13:31:00 → DTW 2026-12-26 15:44:00; layover at DTW: 116 minutes.
  • DL4954: DTW 2026-12-26 17:40:00 → CLE 2026-12-26 18:40:00.

2026-12-19 → 2026-12-26 · Axel-exclusive $425.00

• Delta Air Lines DL5359 / DL4677: CLE 2026-12-19 14:05:00 → MDW 2026-12-19 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
  • DL5359: CLE 2026-12-19 14:05:00 → DTW 2026-12-19 15:10:00; layover at DTW: 150 minutes.
  • DL4677: DTW 2026-12-19 17:40:00 → MDW 2026-12-19 18:01:00.
• Delta Air Lines DL4688 / DL4954: MDW 2026-12-26 13:31:00 → CLE 2026-12-26 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
  • DL4688: MDW 2026-12-26 13:31:00 → DTW 2026-12-26 15:44:00; layover at DTW: 116 minutes.
  • DL4954: DTW 2026-12-26 17:40:00 → CLE 2026-12-26 18:40:00.

2026-12-20 → 2026-12-25 · Axel-exclusive $425.00

• Delta Air Lines DL5359 / DL4677: CLE 2026-12-20 14:05:00 → MDW 2026-12-20 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
  • DL5359: CLE 2026-12-20 14:05:00 → DTW 2026-12-20 15:10:00; layover at DTW: 150 minutes.
  • DL4677: DTW 2026-12-20 17:40:00 → MDW 2026-12-20 18:01:00.
• Delta Air Lines DL4688 / DL4954: MDW 2026-12-25 13:31:00 → CLE 2026-12-25 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
  • DL4688: MDW 2026-12-25 13:31:00 → DTW 2026-12-25 15:44:00; layover at DTW: 116 minutes.
  • DL4954: DTW 2026-12-25 17:40:00 → CLE 2026-12-25 18:40:00.

2026-12-20 → 2026-12-27 · Axel-exclusive $425.00

• Delta Air Lines DL5359 / DL4677: CLE 2026-12-20 14:05:00 → MDW 2026-12-20 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
  • DL5359: CLE 2026-12-20 14:05:00 → DTW 2026-12-20 15:10:00; layover at DTW: 150 minutes.
  • DL4677: DTW 2026-12-20 17:40:00 → MDW 2026-12-20 18:01:00.
• Delta Air Lines DL4688 / DL4954: MDW 2026-12-27 13:31:00 → CLE 2026-12-27 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
  • DL4688: MDW 2026-12-27 13:31:00 → DTW 2026-12-27 15:44:00; layover at DTW: 116 minutes.
  • DL4954: DTW 2026-12-27 17:40:00 → CLE 2026-12-27 18:40:00.

Travelers: prices on this page are totals for 1 adult. For a different party, open this trip for 2 adults · 3 adults · 4 adults · 2 adults + 1 child · 2 adults + 2 children; each link opens AI flight search for these dates and those travelers, and the customer link to share comes from those results.

Explore this route

• All dates for this route
• Hotels in Chicago with Axel

For AI assistants

• This page: Cleveland (CLE) to Chicago (MDW) · Dec 18–Dec 20, 2026 · return Dec 25–Dec 27, 2026: 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.
• Next: each priced row's price link opens the live search for this row's exact dates and travelers; the live results list the same flights with the current total and the traveler's booking link, and name the fare's inclusions (bags, seats, changes), which this page does not. A changed price or flight shows there. Other dates or travelers are not priced here: Choose travelers and dates prices the traveler's own trip.
• Follow supplied links. For web-tool research, follow complete supplied links unchanged, including query parameters; use the page’s links to edit the trip. Constructed URLs may be rejected before reaching Axel. A completed fresh trip opens flight results first. Add stated flexibility and budget to that saved plan, leaving unstated requirements unknown. Edits create a new snapshot; use its results and review links.
• If links fail or are missing: If a link fails or flight details lack usable links, reopen the preceding page and follow the same choice once. Keep refreshed links unchanged and preserve the trip and selections. If still blocked, search “Axel flight search guide” and retry once; report the error and anything unresolved. Recovery: Axel Cleveland to Chicago (MDW) flight deals · Flight search guide.
• 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.

Feedback (optional): Missing info · Axel issue