Flights from San Juan 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 San Juan: Chicago (American, United, Frontier), Chicago (Southwest), Minneapolis (Delta, Sun Country), Detroit (Delta), Saint Louis (Southwest), Kansas City (Southwest) and Columbus (Southwest). One stop via Fort Lauderdale: Cleveland. No nonstop seen to Cincinnati, Indianapolis, Milwaukee and Pittsburgh on the dates searched recently.

Axel's pick: Chicago, nonstop on American, United and Frontier and the lowest fare saved for these dates, $204.

Where to fly from San Juan 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 $161 · Chicago $204 · Columbus $205

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Flights from San Juan

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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 San Juan

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 · American, United, Frontier$204 (airline $216)Dec 3–6, 2026Check prices
Chicago (MDW)Chicago Midway, the close-in airportNonstop · SouthwestNo 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 CountryNo matching fare savedDec 3 – Dec 6, 2026 (suggested)Search these dates
Detroit (DTW)Detroit's music history and the Motor City's comebackNonstop · DeltaNo matching fare savedDec 3 – Dec 6, 2026 (suggested)Search these dates
Saint Louis (STL)St. Louis' Gateway Arch and barbecueNonstop · SouthwestNo matching fare savedDec 3 – Dec 6, 2026 (suggested)Search these dates
Kansas City (MCI)Kansas City's barbecue and jazzNonstop · SouthwestNo matching fare savedDec 3 – Dec 6, 2026 (suggested)Search these dates
Cleveland (CLE)Cleveland's Rock and Roll Hall of Fame and lakefront1 stop via Fort Lauderdale$161 (airline $170)Dec 3–6, 2026Check prices
Columbus (CMH)Columbus' breweries and Short North arts districtNonstop · Southwest$205 (airline $217)Dec 3–6, 2026Check prices
Cincinnati (CVG)Cincinnati's riverfront and chiliNo nonstop seenNo matching fare savedDec 3 – Dec 6, 2026 (suggested)Search these dates
Indianapolis (IND)Indianapolis' speedway and canal walkNo nonstop seenNo matching fare savedDec 3 – Dec 6, 2026 (suggested)Search these dates
Milwaukee (MKE)Milwaukee's breweries and lakefront festivalsNo nonstop seenNo matching fare savedDec 3 – Dec 6, 2026 (suggested)Search these dates
Pittsburgh (PIT)Pittsburgh's rivers, inclines and museumsNo nonstop seenNo 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 San Juan to the Midwest for 4 days. Round-trip fares from San Juan 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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