Destination intelligence

Cheapest routes to Chicago

Compare origins fast and spot the lowest fares to Chicago.

Start with Chicago and compare origins side by side. You will see the lowest fare and a typical price for context.

Best origin San José (SJO)

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Lowest fares now

Live

San José

SJO1 stopOut 11h 16mBack 13h 49m

€255

Saint Vincent

SVD2 stopsOut 32h 51mBack 29h 15m

€428

Brussels

BRU1 stopOut 12h 50mBack 12h 20m

€474

Lowest €255Typical €294High €2,316

Lowest

€255^*

Typical

€294^*

High

€2,316^*

The lowest fare is €255 with a typical price around €294. Current fares sit near the typical range. High fares reach about €2,316. Use the range as a calm reference when you compare routes.

Photo by Pedro Lastra on Unsplash

Destination profile

Chicago

United States

Routes to Chicago that the flyX community keeps on its radar.

Cheapest from

15 countries

Typical price

€668^*

Best origin

San José (SJO)

Updated 1h ago • Recently checked^*

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Best overall deal

€255

13% below typical

Best origin

San José (SJO)

Closest strong starting point in the mix.

Typical price range

€294

€255 → €2,316

What is moving

Price radar notes for Chicago.

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Cheapest by origin country

Best origin San José (SJO)Back to homepage

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Costa Rica

San José (SJO)

View deals from Costa Rica

1 stopsOut 11h 16mBack 13h 49m6 Mar → 10 MarChecked Updated 19h ago

€255^*Best originTypical €294Cross-border escape

View deal details Clear for takeoff

Booking opens on Kiwi.com.

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St. Vincent & Grenadines

Saint Vincent (SVD)

View deals from St. Vincent & Grenadines

2 stopsOut 32h 51mBack 29h 15m4 Mar → 18 MarChecked Updated 12h ago

€428^*Typical €451Cross-border escape

View deal details Clear for takeoff

Booking opens on Kiwi.com.

Affiliate disclosure

Belgium

Brussels (BRU)

View deals from Belgium

1 stopsOut 12h 50mBack 12h 20m13 Apr → 21 AprChecked Updated 6h ago

€474^*Typical €488Cross-border escape

View deal details Clear for takeoff

Booking opens on Kiwi.com.

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Spain

Madrid (MAD)

View deals from Spain

DirectOut 9h 55mBack 8h 10m25 Feb → 3 MarChecked Updated 11h ago

€479^*Typical €509Cross-border escapeoneworld

View deal details Clear for takeoff

Booking opens on Kiwi.com.

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Dominica

Saint Andrew Parish (DOM)

View deals from Dominica

3 stopsOut 36mBack 56m26 Feb → 5 MarChecked Updated 11h ago

€532^*Cross-border escape

View deal details Clear for takeoff

Booking opens on Kiwi.com.

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Haiti

Cap-Haïtien (CAP)

View deals from Haiti

1 stopsOut 9h 18mBack 14h 37m19 Feb → 23 FebChecked Updated 18h ago

€571^*Typical €571Cross-border escape

View deal details Clear for takeoff

Booking opens on Kiwi.com.

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Lebanon

Beirut (BEY)

View deals from Lebanon

2 stopsOut 43mBack 19h 0m5 May → 12 MayChecked Updated 11h ago

€657^*Typical €678Cross-border escape

View deal details Clear for takeoff

Booking opens on Kiwi.com.

Affiliate disclosure

St. Lucia

Saint Lucia (UVF)

View deals from St. Lucia

2 stopsOut 19h 13mBack 18h 41m4 Jun → 14 JunChecked Updated 15h ago

€668^*Typical €692Cross-border escape

View deal details Clear for takeoff

Booking opens on Kiwi.com.

Affiliate disclosure

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