Cheap Flights from Chicago

10 routes checked daily, from $627 round trip, checked Oct 27

Prices last checked: Oct 27, 2026

Destination guides from Chicago

Where ORD has a tracked route. Each guide compares US departure cities, best months and entry rules.

Flights to Grand Cayman (GCM)Flights to Reykjavik (KEF)Flights to Montego Bay (MBJ)Flights to Venice (VCE)Flights to Barbados (BGI)Flights to London (LHR)Flights to Lisbon (LIS)Flights to Tel Aviv (TLV)Flights to Bangkok (BKK)Flights to Manila (MNL)Flights to Colombo (CMB)Flights to Jakarta (CGK)

Cheapest live fares from Chicago right now

Real fares from our daily check, cheapest first. Each is for the month shown; set an alert to hear when it drops.

Biggest movers this week from Chicago

Median fare over the last seven daily checks against the seven before, per route. Drops first.

RouteLast 7 daysChange
ORD to BKKBangkok$1,569down 4%
ORD to KEFReykjavik$630flat
ORD to MNLManila$2,007up 2%
ORD to TLVTel Aviv$1,124up 2%
ORD to LISLisbon$862up 3%
ORD to MBJMontego Bay$606up 9%

Observed fares from Wildly's daily check, snapshot Oct 27. Round trip, economy, for the sample dates shown; not an estimate and not a bookable offer. How we check fares

Observed fares from Chicago by region

Every route from Chicago with a fare from the last week, grouped by where it goes. Each destination has its own guide comparing US departure cities and best months.

Europe

Caribbean

Asia

Africa & Middle East

Observed fares from Wildly's daily check, snapshot Oct 27. Round trip, economy, for the sample dates shown; not an estimate and not a bookable offer. How we check fares

Lowest estimated prices from Chicago (estimate)

Estimate: modelled from route distance and region, not an observed fare. Observed fares, where we have them, are in the sections above.

MTY
Monterrey
Mexico
Est. $111
round trip
~4h flight time
NAS
Nassau
Bahamas
Est. $111
round trip
~4h flight time
CUN
Cancun
Mexico
Est. $122
round trip
~4h flight time
GCM
Grand Cayman
Cayman Islands
Est. $136
round trip
~4h flight time
MEX
Mexico City
Mexico
Est. $142
round trip
~4h flight time
MBJ
Montego Bay
Jamaica
Est. $145
round trip
~4h flight time
GDL
Guadalajara
Mexico
Est. $146
round trip
~4h flight time
PVR
Puerto Vallarta
Mexico
Est. $150
round trip
~5h flight time
KIN
Kingston
Jamaica
Est. $150
round trip
~5h flight time
SJD
Los Cabos
Mexico
Est. $152
round trip
~5h flight time

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All destinations from Chicago (estimates)

Estimate: modelled from route distance and region, not an observed fare. Observed fares, where we have them, are in the sections above.

DestinationCountryRegionEst. PriceFlight Time
MTYMonterreyMexicocentral america-caribbean$111~4h
NASNassauBahamascentral america-caribbean$111~4h
CUNCancunMexicocentral america-caribbean$122~4h
GCMGrand CaymanCayman Islandscentral america-caribbean$136~4h
MEXMexico CityMexicocentral america-caribbean$142~4h
MBJMontego BayJamaicacentral america-caribbean$145~4h
GDLGuadalajaraMexicocentral america-caribbean$146~4h
PVRPuerto VallartaMexicocentral america-caribbean$150~5h
KINKingstonJamaicacentral america-caribbean$150~5h
SJDLos CabosMexicocentral america-caribbean$152~5h
SDQSanto DomingoDominican Republiccentral america-caribbean$164~5h
PUJPunta CanaDominican Republiccentral america-caribbean$167~5h
SJUSan JuanPuerto Ricocentral america-caribbean$174~5h
STTSt. ThomasUS Virgin Islandscentral america-caribbean$178~5h
SXMSt. MaartenSint Maartencentral america-caribbean$185~5h
AUAArubaArubacentral america-caribbean$194~6h
ANUAntiguaAntigua and Barbudacentral america-caribbean$194~6h
CURCuracaoCuracaocentral america-caribbean$198~6h
UVFSt. LuciaSaint Luciacentral america-caribbean$213~6h
BGIBarbadosBarbadoscentral america-caribbean$221~6h
POSTrinidadTrinidad and Tobagocentral america-caribbean$227~6h
KEFReykjavikIcelandeurope$247~7h
DUBDublinIrelandeurope$308~8h
GLAGlasgowUnited Kingdomeurope$308~8h
EDIEdinburghUnited Kingdomeurope$311~8h
MANManchesterUnited Kingdomeurope$321~9h
BHXBirminghamUnited Kingdomeurope$325~9h
OPOPortoPortugaleurope$331~9h
LHRLondonUnited Kingdomeurope$332~9h
LISLisbonPortugaleurope$336~9h
OSLOsloNorwayeurope$339~9h
AMSAmsterdamNetherlandseurope$345~9h
FAOFaroPortugaleurope$346~9h
CDGParisFranceeurope$348~9h
BRUBrusselsBelgiumeurope$349~9h
MADMadridSpaineurope$352~9h
SVQSevilleSpaineurope$353~9h
DUSDusseldorfGermanyeurope$354~9h
HAMHamburgGermanyeurope$357~9h
CPHCopenhagenDenmarkeurope$358~10h
ARNStockholmSwedeneurope$358~10h
AGPMalagaSpaineurope$361~10h
FRAFrankfurtGermanyeurope$364~10h
LYSLyonFranceeurope$367~10h
GVAGenevaSwitzerlandeurope$369~10h
BCNBarcelonaSpaineurope$371~10h
BERBerlinGermanyeurope$371~10h
ZRHZurichSwitzerlandeurope$372~10h
HELHelsinkiFinlandeurope$372~10h
MRSMarseilleFranceeurope$375~10h
TLLTallinnEstoniaeurope$375~10h
IBZIbizaSpaineurope$376~10h
MXPMilanItalyeurope$379~10h
PMIPalma de MallorcaSpaineurope$379~10h
MUCMunichGermanyeurope$380~10h
PRGPragueCzech Republiceurope$381~10h
NCENiceFranceeurope$381~10h
RIXRigaLatviaeurope$383~10h
LEDSt. PetersburgRussiaeurope$385~10h
VCEVeniceItalyeurope$392~10h
WAWWarsawPolandeurope$393~10h
FLRFlorenceItalyeurope$394~10h
VIEViennaAustriaeurope$395~10h
VNOVilniusLithuaniaeurope$395~10h
LJULjubljanaSloveniaeurope$396~10h
KRKKrakowPolandeurope$397~10h
BTSBratislavaSlovakiaeurope$397~10h
ZAGZagrebCroatiaeurope$402~11h
FCORomeItalyeurope$404~11h
BUDBudapestHungaryeurope$406~11h
SPUSplitCroatiaeurope$411~11h
NAPNaplesItalyeurope$415~11h
SVOMoscowRussiaeurope$416~11h
SJJSarajevoBosnia and Herzegovinaeurope$417~11h
BEGBelgradeSerbiaeurope$419~11h
DBVDubrovnikCroatiaeurope$421~11h
TGDPodgoricaMontenegroeurope$425~11h
TIATiranaAlbaniaeurope$431~11h
MLTMaltaMaltaeurope$434~11h
SKPSkopjeNorth Macedoniaeurope$434~11h
OTPBucharestRomaniaeurope$437~11h
SOFSofiaBulgariaeurope$437~11h
SKGThessalonikiGreeceeurope$444~12h
ATHAthensGreeceeurope$458~12h
ISTIstanbulTurkeyeurope$459~12h
SAWIstanbul SabihaTurkeyeurope$462~12h
MYKMykonosGreeceeurope$465~12h
JTRSantoriniGreeceeurope$470~12h
AYTAntalyaTurkeyeurope$484~13h
LCALarnacaCypruseurope$501~13h
NRTTokyoJapanasia$579~14h
HNDTokyo HanedaJapanasia$582~14h
TLVTel AvivIsraelmiddle east$596~13h
KIXOsakaJapanasia$600~14h
ICNSeoulSouth Koreaasia$604~14h
PEKBeijingChinaasia$607~14h
PVGShanghaiChinaasia$651~15h
TPETaipeiTaiwanasia$688~16h
DELDelhiIndiaasia$690~16h
KTMKathmanduNepalasia$703~16h
CANGuangzhouChinaasia$714~16h
SZXShenzhenChinaasia$717~17h
HKGHong KongHong Kongasia$719~17h
HANHanoiVietnamasia$738~17h
BOMMumbaiIndiaasia$743~17h
MNLManilaPhilippinesasia$751~17h
CNXChiang MaiThailandasia$759~17h
VTEVientianeLaosasia$762~17h
CEBCebuPhilippinesasia$767~18h
DADDa NangVietnamasia$767~18h
RGNYangonMyanmarasia$773~18h
BLRBangaloreIndiaasia$787~18h
REPSiem ReapCambodiaasia$789~18h
BKKBangkokThailandasia$791~18h
MAAChennaiIndiaasia$792~18h
PNHPhnom PenhCambodiaasia$800~18h
SGNHo Chi Minh CityVietnamasia$802~18h
HKTPhuketThailandasia$828~19h
CMBColomboSri Lankaasia$828~19h
MLEMaleMaldivesasia$836~19h
PENPenangMalaysiaasia$844~19h
KULKuala LumpurMalaysiaasia$858~20h
SINSingaporeSingaporeasia$864~20h
DPSBaliIndonesiaasia$901~20h
CGKJakartaIndonesiaasia$906~21h

Featured route estimates from Chicago (estimate)

Estimate: modelled from route distance and region, not an observed fare. Observed fares, where we have them, are in the sections above.

ROUTE ESTIMATE
ORD → MTY
Monterrey
Est. $111
estimated round trip
View Route
ROUTE ESTIMATE
ORD → NAS
Nassau
Est. $111
estimated round trip
View Route
ROUTE ESTIMATE
ORD → CUN
Cancun
Est. $122
estimated round trip
View Route

Best Time to Fly from Chicago

Based on seasonal patterns across popular destinations, the best months to find deals from Chicago are typically January, February, March, April.

These months tend to offer the best combination of good weather at your destination and lower airfare demand.

About O'Hare International

O'Hare is United's second-largest hub after Houston, making it a powerhouse for transatlantic and transpacific flights. You'll find competitive pricing on European routes because United, American, and Delta all fight for market share here. The airport is modernizing aggressively—the new Terminal 5 (opened 2024) is genuinely pleasant, though older terminals still have the tired-airport vibe. O'Hare handles 84+ million passengers annually, so expect crowds during peak hours (6-9am, 4-7pm), but the airport's been investing in TSA PreCheck lanes and Clear kiosks, making security manageable if you're enrolled.

Terminals & Airlines

Terminal 1 (American/partners), Terminal 2 (international carriers including Lufthansa, Air France, British Airways, Swiss), Terminal 3 (United hub—massive, confusing, but has best food options), Terminal 5 (new, modern, houses some United flights and partners), Terminal C (regional/low-cost carriers, Southwest when it operates). Terminal 2 is worth targeting for European carriers—newer, less chaotic. Terminal 3 is unavoidable for most United flights but plan extra time for connections.

Getting to the Airport

CTA Blue Line (24/7, $5 one-way, 40-45 min from Loop/downtown Chicago during normal traffic, often faster than driving)—board at any downtown station, runs directly to all terminals. Rideshare (Uber/Lyft, $28-42 during off-peak, $50-75 during rush hour 6-10am or 3-7pm from downtown, 25-40 min depending on traffic). Taxi flat rate $42 from downtown Loop, 35-50 min. Rental car pickup in Terminal 1 or off-site shuttles available. Best option: CTA Blue Line if traveling light and flexible on time; Uber/Lyft if arriving after 10pm when Blue Line gets sketchy.

Parking

Economy Lot A/B: $17/day (10-min walk or free shuttle). Garage parking (covered): $19/day. Valet at terminal: $32/day. Pro move: book through SpotHero or ParkWhiz 2+ weeks ahead for $8-12/day at nearby off-airport lots with free airport shuttle—saves $5-10/day and less hassle than economy lot. Cell phone lot is free for 15 min while waiting for pickup.

Airlines at ORD

United (major hub)American AirlinesDeltaSouthwestLufthansaAir FranceBritish AirwaysKLMFinnairSwiss InternationalANA (All Nippon Airways)Japan AirlinesKorean AirVirgin AtlanticIcelandairTurkish AirlinesAir CanadaWestJetSpirit AirlinesFrontier AirlinesAllegiant Air

Pro Tips for Flying from Chicago

1

United runs 3+ daily flights to London (LHR, LGW, STN) from ORD—prices are genuinely competitive because American and Delta also fly the route heavily. Check all three London airports before booking; Stansted is sometimes $80-120 cheaper but adds an hour to ground transport.

2

ORD to Dublin (DUB) is a sweet spot: 5-6 daily flights across United/American/Aer Lingus, and the route rarely gets expensive. Book 4-6 weeks ahead and you'll find sub-$400 roundtrip transatlantic fares regularly.

3

Terminal 3 (United) has a hidden gem: the United Club in concourse B has shower suites ($35 for 60 min, free for Elite members). If you have a long layover on a hot day, it's worth the cost.

4

Finnair and other Nordic carriers use ORD heavily for Asia connections via Helsinki—often cheaper than United's Asia routes, especially to Tokyo and Bangkok. Compare Finnair/ANA joint fares before assuming United is the best option.

5

The TSA PreCheck line at ORD in Terminal 3 can still hit 20+ min during 6-9am. If not Pre/Clear enrolled, fly out 11am-2pm or after 7pm for sub-10 min security waits.

Cheapest regions from Chicago (estimate)

Estimate: modelled from route distance and region, not an observed fare. Observed fares, where we have them, are in the sections above.

RegionEst. Avg PriceBest Month
mexico$280september
caribbean$320august
central America$340september
europe$480may
south America$580april
middle East$620october
asia$650september
africa$750november
oceania$820september

Nearby Airports to Consider

MDWChicago Midway International
25 min southwest from downtown
Southwest flights, budget carriers (Spirit, Frontier). Sometimes 10-15% cheaper for Caribbean routes due to Southwest's presence. Skip ORD if you're flexible and flying Southwest.
RFDChicago Rockford International
1 hour northwest of Chicago
Rarely worth the extra drive; only consider if you find a flight $150+ cheaper and you have a car.

Frequently Asked Questions

What are the cheapest international flights from Chicago?

In our daily check the lowest round trips from ORD were Grand Cayman (GCM) at $627 for December, Reykjavik (KEF) at $630 for December, Montego Bay (MBJ) at $658 for December, checked Oct 27. Fares change daily; each route page has the current figure.

When is the best time to fly from Chicago?

Based on seasonal patterns, the best months to find deals from Chicago are typically January, February, March, April. These periods tend to offer a balance of favorable weather at popular destinations and lower demand for flights.

How far in advance should I book flights from Chicago?

For international flights from Chicago, booking 6–12 weeks in advance typically yields the best prices. For peak summer travel (June–August) and holiday periods, booking 3–6 months early is recommended.

What airports serve Chicago?

Chicago is served by O'Hare International (ORD).

How many international destinations can I fly to from Chicago?

Wildly lists 125+ international destinations from Chicago. These span regions including Europe, Asia, the Caribbean, South America, and beyond. Browse all routes to find your target destination.

Flights from Chicago by Budget

Filter routes from Chicago by your price target:

Under $200 (18 routes)Under $300 (22 routes)Under $400 (67 routes)Under $500 (89 routes)Under $600 (94 routes)Under $800 (116 routes)Under $1000 (125 routes)

Flights from Chicago by Region

Europe
69 routes →
Asia
34 routes →
Central America & Caribbean
21 routes →
Middle East
1 route →

Related Reading

When to Book Flights for the Cheapest Price
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How to Find Cheap Flights: The Complete Guide
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