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
Best cards for this trip
Open Sapphire Preferred + World of Hyatt. Park Hyatt Chicago (Cat 6, 35K/night) on Magnificent Mile — bonuses cover 4 nights + RT flight.
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