US · city
Chicago, IL
United States
Architecture cruises, deep-dish pizza, Cubs at Wrigley, lakefront jogging
May-Oct ideal (65-85°F). Famous "Windy City" winters can hit -10°F with wind chill. Summer humid but lakefront cools.
When to visit
Award flights from the US
Economy
Chase Ultimate Rewards
via Southwest Rapid Rewards
+ $30 taxes
Chase UR → Southwest LGA-MDW direct
American AAdvantage
+ $20 taxes
AA economy JFK-ORD
Business / First
American AAdvantage
+ $20 taxes
AA business JFK-ORD
Cash equivalent: economy ~$250 · business ~$900 roundtrip from NYC
Award hotels
Park Hyatt Chicago
Hyatt
Cat 6 — Magnificent Mile luxury, top-floor restaurant.
Hyatt Centric The Loop Chicago
Hyatt
Cat 5 — boutique Loop, walking to Millennium Park.
Hyatt Regency Chicago
Hyatt
Cat 4 — large convention hotel, Riverwalk.
Thompson Chicago
Hyatt
Cat 6 — Gold Coast/River North boutique.
What to see & do
Art Institute of Chicago
World-class collection — American Gothic, Nighthawks, Monet's Water Lilies.
Architecture River Cruise
90-min boat tour past Chicago's most famous skyscrapers. Best of the city.
Millennium Park + The Bean
Cloud Gate sculpture is iconic. Free summer concerts at Pritzker Pavilion.
Wrigley Field
Watch Cubs in 1914 ballpark — ivy walls, Old Style beer, Wrigleyville bars after.
Lou Malnati's / Giordano's
Deep-dish pizza pilgrimage. Different style at each — try both, settle the debate.
Lakefront Bike Trail
18 miles of paved trail along Lake Michigan. Rent bikes anywhere downtown.
Monthly weather
| Month | Low | High | Rain |
|---|---|---|---|
| Jan | 18°F | 31°F | |
| Feb | 22°F | 35°F | |
| Mar | 31°F | 45°F | |
| Apr | 42°F | 58°F | |
| May | 53°F | 70°F | |
| Jun | 63°F | 79°F | |
| Jul | 69°F | 84°F | |
| Aug | 68°F | 82°F | |
| Sep | 60°F | 75°F | |
| Oct | 47°F | 63°F | |
| Nov | 35°F | 49°F | |
| Dec | 22°F | 35°F |
Best cards for this trip
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