Flights from Orlando to the Midwest for 4 days

Four days is Chicago done properly, or a city with a day out: Minneapolis with the North Shore, Cleveland with the Rock Hall and the lake, Detroit with Ann Arbor. Summer and early autumn for the weather.

Nonstop from Orlando: Chicago (Frontier, American, United · 3h 09m), Chicago (Southwest, Frontier), Minneapolis (Delta, Sun Country, Frontier), Detroit (Frontier, Delta, Southwest), Saint Louis (Frontier, Southwest), Kansas City (Southwest, Frontier), Cleveland (Frontier, United, Southwest · 2h 30m), Columbus (Frontier, Southwest · 2h 20m), Cincinnati (Frontier, Delta), Indianapolis (Southwest, Frontier), Milwaukee (Southwest, Frontier) and Pittsburgh (Frontier, Southwest, Delta).

Axel's pick: Cleveland, nonstop on Frontier, United and Southwest and the lowest fare saved for these dates, $107.

Where to fly from Orlando to the Midwest for 4 days: round trips of 3 to 4 nights to Chicago, Minneapolis, Detroit, Saint Louis, Kansas City and Cleveland and more. Pick a destination to see every date, or search your own dates in one tap.

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Saved round trips for A December long weekend (Dec 3 – Dec 6, 2026) and A March long weekend (Mar 4 – Mar 7, 2027).

Cheapest right now: Cleveland $107 · Columbus $127 · Chicago $168

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Flights from Orlando

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The Midwest for 4 days from other cities

Fares observed October 28, 2026. USD for the travelers shown. Search a trip for current prices.

Where to go from Orlando

Round-trip totals · Economy · USD · 1 adult unless shown. "From" is a starting total: you pick the return in Axel. Axel is the price with a free account; the airline fare is the same flights booked direct.

DestinationWhy goFlightsAxelDates
Chicago (ORD)Chicago's architecture, lakefront and deep-dishNonstop · Frontier, American, United · 3h 09m$168 (airline $177)Dec 3–6, 2026Check prices
Chicago (MDW)Chicago Midway, the close-in airportNonstop · Southwest, FrontierNo matching fare savedDec 3 – Dec 6, 2026 (suggested)Search these dates
Minneapolis (MSP)Minneapolis and St. Paul's lakes and the Mall of AmericaNonstop · Delta, Sun Country, FrontierNo matching fare savedDec 3 – Dec 6, 2026 (suggested)Search these dates
Detroit (DTW)Detroit's music history and the Motor City's comebackNonstop · Frontier, Delta, SouthwestNo matching fare savedDec 3 – Dec 6, 2026 (suggested)Search these dates
Saint Louis (STL)St. Louis' Gateway Arch and barbecueNonstop · Frontier, SouthwestNo matching fare savedDec 3 – Dec 6, 2026 (suggested)Search these dates
Kansas City (MCI)Kansas City's barbecue and jazzNonstop · Southwest, FrontierNo matching fare savedDec 3 – Dec 6, 2026 (suggested)Search these dates
Cleveland (CLE)Cleveland's Rock and Roll Hall of Fame and lakefrontNonstop · Frontier, United, Southwest · 2h 30m$107 (airline $113)Dec 3–6, 2026Check prices
Columbus (CMH)Columbus' breweries and Short North arts districtNonstop · Frontier, Southwest · 2h 20m$127 (airline $134)Dec 3–6, 2026Check prices
Cincinnati (CVG)Cincinnati's riverfront and chiliNonstop · Frontier, DeltaNo matching fare savedDec 3 – Dec 6, 2026 (suggested)Search these dates
Indianapolis (IND)Indianapolis' speedway and canal walkNonstop · Southwest, FrontierNo matching fare savedDec 3 – Dec 6, 2026 (suggested)Search these dates
Milwaukee (MKE)Milwaukee's breweries and lakefront festivalsNonstop · Southwest, FrontierNo matching fare savedDec 3 – Dec 6, 2026 (suggested)Search these dates
Pittsburgh (PIT)Pittsburgh's rivers, inclines and museumsNonstop · Frontier, Southwest, DeltaNo matching fare savedDec 3 – Dec 6, 2026 (suggested)Search these dates

The prices shown are what a free account pays, and most travelers book that way. Membership is optional and takes the same flights lower. Live search shows the same free-account price.

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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

For AI assistants

  • This page: Flights from Orlando to the Midwest for 4 days. Round-trip fares from Orlando to the Midwest for 4 days: Chicago, Minneapolis, Detroit, Saint Louis, Kansas City and Cleveland and more, for stays of 3 to 4 nights. The cheapest saved fare for each destination, and a link to search your own dates.
  • 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.
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