United States
Cheap flights to Chicago
I watch round trips to Chicago from 40 US airports. When one drops 40% or more below what it usually costs, members hear about it.
- Fares compared with the route's usual price
- Every deal checked live before it's sent
- You book directly with the airline
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This week
Lowest fares to Chicago by airport
Round-trip economy fares Pounce spotted in the last 7 days, for trips in the next 6 months. They come from recent searches, not live prices, and change fast. Members get deals that are checked live before they're sent.
| From | Lowest seen | Typical | Cheapest month |
|---|---|---|---|
| Baltimore (BWI) | $72 | $72 | Nov 2026 |
| Dallas/Fort Worth (DFW) | $90 | $95 | Nov 2026 |
| Atlanta (ATL) | $107 | $147 | Nov 2026 |
| Fort Lauderdale (FLL) | $108 | $150 | Dec 2026 |
| St. Louis (STL) | $133 | $190 | Nov 2026 |
| Los Angeles (LAX) | $134 | $205 | Dec 2026 |
| Austin (AUS) | $141 | $170 | Nov 2026 |
| Las Vegas (LAS) | $143 | $143 | Nov 2026 |
| Minneapolis (MSP) | $143 | $143 | Nov 2026 |
| Tampa (TPA) | $143 | $245 | Nov 2026 |
| Nashville (BNA) | $146 | $146 | Nov 2026 |
| Newark (EWR) | $147 | $205 | Nov 2026 |
| Houston (IAH) | $149 | $149 | Nov 2026 |
| Miami (MIA) | $155 | $180 | Nov 2026 |
| Seattle (SEA) | $155 | $251 | Feb 2027 |
| New York LaGuardia (LGA) | $161 | $196 | Nov 2026 |
| New Orleans (MSY) | $163 | $185 | Jan 2027 |
| Charlotte (CLT) | $168 | $168 | Nov 2026 |
| Phoenix (PHX) | $180 | $180 | Nov 2026 |
| New York JFK (JFK) | $187 | $205 | Nov 2026 |
| San Jose (SJC) | $188 | $240 | Dec 2026 |
| Washington Dulles (IAD) | $192 | $192 | Nov 2026 |
| Boston (BOS) | $194 | $205 | Nov 2026 |
| San Francisco (SFO) | $196 | $229 | Dec 2026 |
| Orlando (MCO) | $207 | $264 | Nov 2026 |
| Philadelphia (PHL) | $212 | $220 | Mar 2027 |
| Raleigh-Durham (RDU) | $217 | $217 | Nov 2026 |
| Oakland (OAK) | $220 | $295 | Dec 2026 |
| Portland (PDX) | $251 | $251 | Nov 2026 |
| San Antonio (SAT) | $260 | $260 | Nov 2026 |
| Denver (DEN) | $263 | $281 | Dec 2026 |
Proof
Past deals to Chicago
Real fares Pounce sent members, next to what each route usually costs. They show up here a few days after members get them.
No past deals to Chicago to show yet. Deals appear here a few days after members get them.
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Flights to Chicago from
- Atlanta (ATL)
- Austin (AUS)
- Nashville (BNA)
- Boston (BOS)
- Baltimore (BWI)
- Charlotte (CLT)
- Washington (DCA)
- Denver (DEN)
- Dallas/Fort Worth (DFW)
- Detroit (DTW)
- Newark (EWR)
- Fort Lauderdale (FLL)
- Honolulu (HNL)
- Washington (IAD)
- Houston (IAH)
- New York (JFK)
- Las Vegas (LAS)
- Los Angeles (LAX)
- New York (LGA)
- Orlando (MCO)
- Miami (MIA)
- Minneapolis (MSP)
- New Orleans (MSY)
- Oakland (OAK)
- Portland (PDX)
- Philadelphia (PHL)
- Phoenix (PHX)
- Pittsburgh (PIT)
- Raleigh-Durham (RDU)
- San Diego (SAN)
- San Antonio (SAT)
- Seattle (SEA)
- San Francisco (SFO)
- San Jose (SJC)
- Salt Lake City (SLC)
- Sacramento (SMF)
- St. Louis (STL)
- Tampa (TPA)
Questions
Flying to Chicago
How cheap can flights to Chicago get?
In the last 7 days, the cheapest round trip to Chicago Pounce spotted from a US airport was $72 from Baltimore (BWI), leaving in Nov 2026. The typical fare from there was $72. Fares change by the hour, so treat these as a guide, not a quote.
Which US airports have the cheapest flights to Chicago?
This week, the lowest fares Pounce saw to Chicago left from Baltimore (BWI) ($72), Dallas/Fort Worth (DFW) ($90), Atlanta (ATL) ($107). It changes week to week, which is why Pounce watches all 40 airports.
How do I get alerts for cheap flights to Chicago?
Join FarePounce with your home airport and choose domestic trips (or both). Pounce sends a fare once it drops 40% or more below the route's usual price and passes a live check.
Can I track only flights to Chicago?
Pounce doesn't track single routes, because the best deals are often to places you weren't searching for. It watches every route from your home airports and sends the ones that are truly cheap.