Cleveland (CLE) to Chicago (MDW), Jan 16, 2027: round trips from $252, one way from $133

Cleveland (CLE) to Chicago (MDW), Jan 16, 2027: round trips from $252, one way from $133 on Axel, checked Oct 29, 2026. Lowest published fares: $252 round trip, Axel-exclusive, Southwest Airlines, nonstop, Jan 16–17, 2027; $133 one way, Axel-exclusive, Southwest Airlines, nonstop, Jan 16, 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 16–17, 2027 · 1 night · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $75 total · 4★ Freehand Chicago, $79 total · 5★ Sofitel Chicago Magnificent Mile, $219 total
• Hotels in Chicago for these nights (Jan 16–18, 2027 · 2 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $150 total · 4★ Freehand Chicago, $151 total · 5★ Sofitel Chicago Magnificent Mile, $442 total
• Hotels in Chicago for these nights (Jan 16–19, 2027 · 3 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $225 total · 4★ Freehand Chicago, $223 total · 5★ Sofitel Chicago Magnificent Mile, $696 total
• Hotels in Chicago for these nights (Jan 16–20, 2027 · 4 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $300 total · 4★ Freehand Chicago, $296 total · 5★ Sofitel Chicago Magnificent Mile, $949 total
• Hotels in Chicago for these nights (Jan 16–21, 2027 · 5 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $385 total · 4★ Freehand Chicago, $368 total · 5★ Sofitel Chicago Magnificent Mile, $1,159 total
• Hotels in Chicago for these nights (Jan 16–22, 2027 · 6 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $468 total · 4★ Freehand Chicago, $440 total · 5★ Sofitel Chicago Magnificent Mile, $1,395 total
• Hotels in Chicago for these nights (Jan 16–23, 2027 · 7 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $543 total · 4★ Freehand Chicago, $518 total · 5★ Sofitel Chicago Magnificent Mile, $1,605 total
• Hotels in Chicago for these nights (Jan 16–24, 2027 · 8 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $618 total · 4★ Freehand Chicago, $597 total · 5★ Sofitel Chicago Magnificent Mile, $2,192 total
• Hotels in Chicago for these nights (Jan 16–25, 2027 · 9 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $701 total · 4★ Freehand Chicago, $668 total · 5★ Nobu Hotel Chicago, $3,545 total
• Hotels in Chicago for these nights (Jan 16–26, 2027 · 10 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $776 total · 4★ Freehand Chicago, $741 total · 5★ Nobu Hotel Chicago, $3,978 total
• Hotels in Chicago for these nights (Jan 16–27, 2027 · 11 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $859 total · 4★ Freehand Chicago, $814 total · 5★ Nobu Hotel Chicago, $4,406 total
• Hotels in Chicago for these nights (Jan 16–28, 2027 · 12 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $934 total · 4★ Freehand Chicago, $886 total · 5★ Nobu Hotel Chicago, $4,793 total
• Hotels in Chicago for these nights (Jan 16–29, 2027 · 13 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,009 total · 4★ Freehand Chicago, $958 total · 5★ Nobu Hotel Chicago, $5,165 total
• Hotels in Chicago for these nights (Jan 16–30, 2027 · 14 nights · 2 adults, 1 room): 3★ The Chicago Hotel Collection River North, $1,093 total · 4★ Freehand Chicago, $1,037 total · 5★ Nobu Hotel Chicago, $5,552 total

All hotels in Chicago

Route overview: Cleveland to Chicago (MDW) flight deals

2027-01-16 · one way · Axel-exclusive $133.00

• Southwest Airlines WN1218: CLE 2027-01-16 08:45:00 → MDW 2027-01-16 09:10:00; nonstop; 85 minutes. Local airport times.

2027-01-16 · one way · Axel-exclusive $185.25

• Delta Air Lines DL5359 / DL4677: CLE 2027-01-16 14:05:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
  • DL5359: CLE 2027-01-16 14:05:00 → DTW 2027-01-16 15:10:00; layover at DTW: 150 minutes.
  • DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.

2027-01-16 → 2027-01-17 · Axel-exclusive $251.76

• Southwest Airlines WN1218: CLE 2027-01-16 08:45:00 → MDW 2027-01-16 09:10:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN4528: MDW 2027-01-17 20:40:00 → CLE 2027-01-17 22:55:00; nonstop; 75 minutes. Local airport times.

2027-01-16 → 2027-01-17 · Axel-exclusive $323.00

• Delta Air Lines DL5359 / DL4677: CLE 2027-01-16 14:05:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
  • DL5359: CLE 2027-01-16 14:05:00 → DTW 2027-01-16 15:10:00; layover at DTW: 150 minutes.
  • DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.
• Delta Air Lines DL4688 / DL4954: MDW 2027-01-17 13:31:00 → CLE 2027-01-17 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
  • DL4688: MDW 2027-01-17 13:31:00 → DTW 2027-01-17 15:44:00; layover at DTW: 116 minutes.
  • DL4954: DTW 2027-01-17 17:40:00 → CLE 2027-01-17 18:40:00.

2027-01-16 → 2027-01-18 · Axel-exclusive $251.76

• Southwest Airlines WN1218: CLE 2027-01-16 08:45:00 → MDW 2027-01-16 09:10:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN1129: MDW 2027-01-18 08:25:00 → CLE 2027-01-18 10:40:00; nonstop; 75 minutes. Local airport times.

2027-01-16 → 2027-01-18 · Axel-exclusive $323.00

• Delta Air Lines DL5359 / DL4677: CLE 2027-01-16 14:05:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
  • DL5359: CLE 2027-01-16 14:05:00 → DTW 2027-01-16 15:10:00; layover at DTW: 150 minutes.
  • DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.
• Delta Air Lines DL4688 / DL4954: MDW 2027-01-18 13:31:00 → CLE 2027-01-18 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
  • DL4688: MDW 2027-01-18 13:31:00 → DTW 2027-01-18 15:44:00; layover at DTW: 116 minutes.
  • DL4954: DTW 2027-01-18 17:40:00 → CLE 2027-01-18 18:40:00.

2027-01-16 → 2027-01-19 · Axel-exclusive $251.76

• Southwest Airlines WN1218: CLE 2027-01-16 08:45:00 → MDW 2027-01-16 09:10:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN1129: MDW 2027-01-19 08:25:00 → CLE 2027-01-19 10:40:00; nonstop; 75 minutes. Local airport times.

2027-01-16 → 2027-01-19 · Axel-exclusive $323.00

• Delta Air Lines DL5359 / DL4677: CLE 2027-01-16 14:05:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
  • DL5359: CLE 2027-01-16 14:05:00 → DTW 2027-01-16 15:10:00; layover at DTW: 150 minutes.
  • DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.
• Delta Air Lines DL4688 / DL4954: MDW 2027-01-19 13:31:00 → CLE 2027-01-19 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
  • DL4688: MDW 2027-01-19 13:31:00 → DTW 2027-01-19 15:44:00; layover at DTW: 116 minutes.
  • DL4954: DTW 2027-01-19 17:40:00 → CLE 2027-01-19 18:40:00.

2027-01-16 → 2027-01-20 · Axel-exclusive $251.76

• Southwest Airlines WN1218: CLE 2027-01-16 08:45:00 → MDW 2027-01-16 09:10:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN1129: MDW 2027-01-20 08:25:00 → CLE 2027-01-20 10:40:00; nonstop; 75 minutes. Local airport times.

2027-01-16 → 2027-01-20 · Axel-exclusive $323.00

• Delta Air Lines DL5359 / DL4677: CLE 2027-01-16 14:05:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
  • DL5359: CLE 2027-01-16 14:05:00 → DTW 2027-01-16 15:10:00; layover at DTW: 150 minutes.
  • DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.
• Delta Air Lines DL4688 / DL4954: MDW 2027-01-20 13:31:00 → CLE 2027-01-20 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
  • DL4688: MDW 2027-01-20 13:31:00 → DTW 2027-01-20 15:44:00; layover at DTW: 116 minutes.
  • DL4954: DTW 2027-01-20 17:40:00 → CLE 2027-01-20 18:40:00.

2027-01-16 → 2027-01-22 · Axel-exclusive $251.76

• Southwest Airlines WN1218: CLE 2027-01-16 08:45:00 → MDW 2027-01-16 09:10:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN1129: MDW 2027-01-22 08:25:00 → CLE 2027-01-22 10:40:00; nonstop; 75 minutes. Local airport times.

2027-01-16 → 2027-01-22 · Axel-exclusive $323.00

• Delta Air Lines DL5359 / DL4677: CLE 2027-01-16 14:05:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
  • DL5359: CLE 2027-01-16 14:05:00 → DTW 2027-01-16 15:10:00; layover at DTW: 150 minutes.
  • DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.
• Delta Air Lines DL4688 / DL4954: MDW 2027-01-22 13:31:00 → CLE 2027-01-22 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
  • DL4688: MDW 2027-01-22 13:31:00 → DTW 2027-01-22 15:44:00; layover at DTW: 116 minutes.
  • DL4954: DTW 2027-01-22 17:40:00 → CLE 2027-01-22 18:40:00.

2027-01-16 → 2027-01-23 · Axel-exclusive $251.76

• Southwest Airlines WN1218: CLE 2027-01-16 08:45:00 → MDW 2027-01-16 09:10:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN1129: MDW 2027-01-23 08:25:00 → CLE 2027-01-23 10:40:00; nonstop; 75 minutes. Local airport times.

2027-01-16 → 2027-01-23 · Axel-exclusive $323.00

• Delta Air Lines DL5359 / DL4677: CLE 2027-01-16 14:05:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
  • DL5359: CLE 2027-01-16 14:05:00 → DTW 2027-01-16 15:10:00; layover at DTW: 150 minutes.
  • DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.
• Delta Air Lines DL4688 / DL4954: MDW 2027-01-23 13:31:00 → CLE 2027-01-23 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
  • DL4688: MDW 2027-01-23 13:31:00 → DTW 2027-01-23 15:44:00; layover at DTW: 116 minutes.
  • DL4954: DTW 2027-01-23 17:40:00 → CLE 2027-01-23 18:40:00.

2027-01-16 → 2027-01-24 · Axel-exclusive $251.76

• Southwest Airlines WN1218: CLE 2027-01-16 08:45:00 → MDW 2027-01-16 09:10:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN4528: MDW 2027-01-24 20:40:00 → CLE 2027-01-24 22:55:00; nonstop; 75 minutes. Local airport times.

2027-01-16 → 2027-01-24 · Axel-exclusive $323.00

• Delta Air Lines DL5359 / DL4677: CLE 2027-01-16 14:05:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
  • DL5359: CLE 2027-01-16 14:05:00 → DTW 2027-01-16 15:10:00; layover at DTW: 150 minutes.
  • DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.
• Delta Air Lines DL4688 / DL4954: MDW 2027-01-24 13:31:00 → CLE 2027-01-24 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
  • DL4688: MDW 2027-01-24 13:31:00 → DTW 2027-01-24 15:44:00; layover at DTW: 116 minutes.
  • DL4954: DTW 2027-01-24 17:40:00 → CLE 2027-01-24 18:40:00.

2027-01-16 → 2027-01-26 · Axel-exclusive $251.76

• Southwest Airlines WN1218: CLE 2027-01-16 08:45:00 → MDW 2027-01-16 09:10:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN1129: MDW 2027-01-26 08:25:00 → CLE 2027-01-26 10:40:00; nonstop; 75 minutes. Local airport times.

2027-01-16 → 2027-01-26 · Axel-exclusive $323.00

• Delta Air Lines DL5359 / DL4677: CLE 2027-01-16 14:05:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
  • DL5359: CLE 2027-01-16 14:05:00 → DTW 2027-01-16 15:10:00; layover at DTW: 150 minutes.
  • DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.
• Delta Air Lines DL4688 / DL4954: MDW 2027-01-26 13:31:00 → CLE 2027-01-26 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
  • DL4688: MDW 2027-01-26 13:31:00 → DTW 2027-01-26 15:44:00; layover at DTW: 116 minutes.
  • DL4954: DTW 2027-01-26 17:40:00 → CLE 2027-01-26 18:40:00.

2027-01-16 → 2027-01-27 · Axel-exclusive $251.76

• Southwest Airlines WN1218: CLE 2027-01-16 08:45:00 → MDW 2027-01-16 09:10:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN1129: MDW 2027-01-27 08:25:00 → CLE 2027-01-27 10:40:00; nonstop; 75 minutes. Local airport times.

2027-01-16 → 2027-01-27 · Axel-exclusive $323.00

• Delta Air Lines DL5359 / DL4677: CLE 2027-01-16 14:05:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
  • DL5359: CLE 2027-01-16 14:05:00 → DTW 2027-01-16 15:10:00; layover at DTW: 150 minutes.
  • DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.
• Delta Air Lines DL4688 / DL4954: MDW 2027-01-27 13:31:00 → CLE 2027-01-27 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
  • DL4688: MDW 2027-01-27 13:31:00 → DTW 2027-01-27 15:44:00; layover at DTW: 116 minutes.
  • DL4954: DTW 2027-01-27 17:40:00 → CLE 2027-01-27 18:40:00.

2027-01-16 → 2027-01-28 · Axel-exclusive $251.76

• Southwest Airlines WN1218: CLE 2027-01-16 08:45:00 → MDW 2027-01-16 09:10:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN4341: MDW 2027-01-28 18:15:00 → CLE 2027-01-28 20:30:00; nonstop; 75 minutes. Local airport times.

2027-01-16 → 2027-01-28 · Axel-exclusive $323.00

• Delta Air Lines DL5359 / DL4677: CLE 2027-01-16 14:05:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
  • DL5359: CLE 2027-01-16 14:05:00 → DTW 2027-01-16 15:10:00; layover at DTW: 150 minutes.
  • DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.
• Delta Air Lines DL4688 / DL4954: MDW 2027-01-28 13:31:00 → CLE 2027-01-28 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
  • DL4688: MDW 2027-01-28 13:31:00 → DTW 2027-01-28 15:44:00; layover at DTW: 116 minutes.
  • DL4954: DTW 2027-01-28 17:40:00 → CLE 2027-01-28 18:40:00.

2027-01-16 → 2027-01-30 · Axel-exclusive $251.76

• Southwest Airlines WN1218: CLE 2027-01-16 08:45:00 → MDW 2027-01-16 09:10:00; nonstop; 85 minutes. Local airport times.
• Southwest Airlines WN1129: MDW 2027-01-30 08:25:00 → CLE 2027-01-30 10:40:00; nonstop; 75 minutes. Local airport times.

2027-01-16 → 2027-01-30 · Axel-exclusive $323.00

• Delta Air Lines DL5359 / DL4677: CLE 2027-01-16 14:05:00 → MDW 2027-01-16 18:01:00; 1 stop(s) via DTW; 296 minutes. Local airport times.
  • DL5359: CLE 2027-01-16 14:05:00 → DTW 2027-01-16 15:10:00; layover at DTW: 150 minutes.
  • DL4677: DTW 2027-01-16 17:40:00 → MDW 2027-01-16 18:01:00.
• Delta Air Lines DL4688 / DL4954: MDW 2027-01-30 13:31:00 → CLE 2027-01-30 18:40:00; 1 stop(s) via DTW; 249 minutes. Local airport times.
  • DL4688: MDW 2027-01-30 13:31:00 → DTW 2027-01-30 15:44:00; layover at DTW: 116 minutes.
  • DL4954: DTW 2027-01-30 17:40:00 → CLE 2027-01-30 18:40:00.

Explore this route

• All dates for this route
• Jan 15, 2027 · Return options
• Jan 17, 2027 · Return options
• Hotels in Chicago with Axel

For AI assistants

• This page: Cleveland (CLE) to Chicago (MDW) · Jan 16, 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.
• Next: each row is one exact trip for this departure (both dates with the year, the total and the time its price was issued); its exact-trip price link opens the live search for those dates and travelers, where the booking link and the current total are. Other durations or travelers are not priced here: Choose travelers and dates prices the requested 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