Long haul · City · Architecture. Compare cheap flights to Chicago from US airports — flight time 2h 49m from Miami International.
Compare flights to Chicago →Chicago is a short-haul destination from the US — around 2h 49m in the air from Miami International (MIA), which makes it a realistic long-weekend trip. Travelers come for Architecture. We track fares from 28 US departure points including Miami International, FLL and Atlanta Hartsfield-Jackson — each has its own comparison page below.
Most travelers aim for May–Oct. Recent round-trip fares start around $37 from Miami International. On the ground, US dollar (USD) is the local currency and English the dominant language — English coverage is solid in tourist quarters and at the airport. Visa: Domestic travel — no visa or ESTA required for US citizens. 4-6 weeks ahead is usually the sweet spot for short-haul fares; last-minute bookings can run two to three times the advance fare.
By Louisa Lowe, Lead Writer · Updated for 2026.
| Departure | Round-trip from | Typical round-trip | |
|---|---|---|---|
| Miami International (MIA) | $37 | $109 | Compare fares → |
| FLL (FLL) | $49 | $101 | Compare fares → |
| Atlanta Hartsfield-Jackson (ATL) | $56 | $109 | Compare fares → |
| PHL (PHL) | $61 | $100 | Compare fares → |
| MSP (MSP) | $62 | $116 | Compare fares → |
| Los Angeles International (LAX) | $73 | $103 | Compare fares → |
| Denver (DEN) | $80 | $117 | Compare fares → |
| Las Vegas (LAS) | $87 | $140 | Compare fares → |
| Orlando (MCO) | $93 | $126 | Compare fares → |
| Boston Logan (BOS) | $95 | $149 | Compare fares → |
| Houston Intercontinental (IAH) | $97 | $159 | Compare fares → |
| Dallas/Fort Worth (DFW) | $98 | $121 | Compare fares → |
| New York JFK (JFK) | $99 | $162 | Compare fares → |
| PHX (PHX) | $106 | $134 | Compare fares → |
| LGA (LGA) | $107 | $152 | Compare fares → |
| Newark (EWR) | $112 | $141 | Compare fares → |
| DCA (DCA) | $115 | $187 | Compare fares → |
| SLC (SLC) | $115 | $156 | Compare fares → |
| DTW (DTW) | $116 | $147 | Compare fares → |
| Washington Dulles (IAD) | $120 | $168 | Compare fares → |
| San Francisco International (SFO) | $121 | $154 | Compare fares → |
| CLT (CLT) | $127 | $136 | Compare fares → |
| BWI (BWI) | $140 | $163 | Compare fares → |
| SAN (SAN) | $142 | $166 | Compare fares → |
| AUS (AUS) | $150 | $190 | Compare fares → |
| Seattle-Tacoma (SEA) | $160 | $194 | Compare fares → |
| TPA (TPA) | $173 | $173 | Compare fares → |
| ANC (ANC) | $293 | $293 | Compare fares → |
Round-trip fares are the lowest and average seen in recent Travelpayouts searches, updated 2026-09-26. Exact prices vary by date — each route page carries the live comparison.
Direct answer. Round-trip flights to Chicago start at around $37, the lowest recent fare on the Miami International–Chicago route. Across the 28 US departures with current fare data, average round-trips run $100–$293.
These figures come from recent Travelpayouts search data, not estimates. The spread between departure airports matters: the same week can price very differently from Miami International, FLL and Atlanta Hartsfield-Jackson, so it pays to compare more than one departure.
The maths to run. On the Miami International route, anything at $65 or under sits in the cheapest quarter of recent fares. Against the $109 route average that keeps $44 per round-trip in your pocket — $176 across four travelers.
Key fact: A round-trip to Chicago at $65 or less counts as a genuinely good deal — that's the cheapest 25% of recent fares on the Miami International route.
Direct answer. CompareFlights tracks 28 US departures for Chicago: Miami International, FLL, Atlanta Hartsfield-Jackson, PHL, MSP, Los Angeles International, Denver, Las Vegas, Orlando, Boston Logan, Houston Intercontinental, Dallas/Fort Worth, New York JFK, PHX, LGA, Newark, DCA, SLC, DTW, Washington Dulles, San Francisco International, CLT, BWI, SAN, AUS, Seattle-Tacoma, TPA and ANC. Each has its own fare page with the live comparison.
Searches hand off to our flight-search partner and you book directly with the airline or agent — we don't resell tickets or add fees. Routes, carriers and schedules change seasonally, so the live search always has the final word.
Key fact: Miami International is currently the cheapest tracked US departure for Chicago, with round-trips from $37.
Direct answer. Book 4-6 weeks ahead, and aim for May–Oct if you want Chicago at its best — that window balances weather and crowds rather than chasing a mythical cheapest day.
Before you commit, the admin: Domestic travel — no visa or ESTA required for US citizens. Currency is US dollar (USD); English is the main language, with English widely understood in tourist areas.
Key fact: Best months to visit Chicago: May–Oct. Flight time from Miami International: about 2h 49m.
Always confirm visa and entry requirements at travel.state.gov before booking.
From Miami International (MIA), nonstop flights to Chicago take approximately 2h 49m. Total journey time depends on your departure airport, any connections, and seasonal headwinds.
CompareFlights tracks 28 US departures for Chicago: Miami International, FLL, Atlanta Hartsfield-Jackson, PHL, MSP, Los Angeles International, Denver, Las Vegas, Orlando, Boston Logan, Houston Intercontinental, Dallas/Fort Worth, New York JFK, PHX, LGA, Newark, DCA, SLC, DTW, Washington Dulles, San Francisco International, CLT, BWI, SAN, AUS, Seattle-Tacoma, TPA and ANC. Each departure has its own fare-comparison page with current prices.
Recent round-trip fares to Chicago start around $37 from Miami International, based on Travelpayouts search data. Anything at $65 or under sits in the cheapest quarter of recent fares.
Domestic travel — no visa or ESTA required for US citizens. Always check travel.state.gov for the latest entry requirements before booking.
The best months to visit Chicago are May–Oct, when conditions are most comfortable for sightseeing and weather is settled.
US dollar (USD) — most major hotels and restaurants in Chicago accept card payments, but cash is useful for smaller establishments and tipping.
English. English is widely understood in tourist areas, hotels, and major restaurants.
