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The same questions, answered side by side for October. We don't pick a winner — the trade-offs are the point.

Chicago, Illinois Chicago Illinois Remove
In October16°C11 rainy days
Flying time3h 55mfrom Los Angeles
Ideal stay3–4 nights
Best forCulture seekers · Foodies · Nightlife
The feel of itBig-shouldered, musical, architecturally serious
Where people stayThe Loop and River Northor Lincoln Park and Old Town
Getting aroundManageable without a car
Money and languageUSDEnglish
AccommodationExpensive

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