AI Trip Planner
Plan a trip with
credit card points
Pick origin + destination + month → see best award flights, top hotels bookable on points, attractions, signature events, and the cards whose welcome bonus would cover the trip. 41 US origin airports, no bank link required.
US
Chicago, IL
Architecture cruises, deep-dish pizza, Cubs at Wrigley, lakefront jogging
Pay in cash
$3,250
$250 flight + $3,000 hotel
Pay with points
191,000 pts
+ $30 taxes & fees
Best card for this trip
Chase World of Hyatt
60K bonus = 1.7 nights at Park Hyatt Chicago + free night cert
Weather in June
☀️ Peak season — ideal time to visit
Air temp
63°–79°F
17°–26°C
Rainfall
moderate
Crowds
Peak
Warm, festival season
Flights — JFK → ORD
EconomyChase Ultimate Rewards
via Southwest Rapid Rewards
JFK → ORD — check direct flights from JFK. Chase UR → Southwest LGA-MDW direct
11K/16K/24K
roundtrip · Wanna Get Away (dynamic)
+ $30 taxes
American AAdvantage
JFK → ORD — check direct flights from JFK. AA economy JFK-ORD
25,000
roundtrip
+ $20 taxes
Open to cover:Sapphire Preferred
Top hotels for your points
Picked for best points value — Hyatt has the only fixed award chart left in major US hotels, so your points stretch the furthest here. Tap each option below for why it stands out.
Park Hyatt Chicago
Hyatt·Luxury flagshipCat 6 — Magnificent Mile luxury, top-floor restaurant.
25K/30K/35K
off / std / peak · Hyatt Cat 7
$600/night cash
5 nights = 175,000 pts (~$3,000 value)
Thompson Chicago
Hyatt·Boutique, diningCat 6 — Gold Coast/River North boutique.
25K/30K/35K
off / std / peak · Hyatt Cat 7
$500/night cash
5 nights = 150,000 pts (~$2,500 value)
Hyatt Regency Chicago
Hyatt·Conventions, familiesCat 4 — large convention hotel, Riverwalk.
17K/20K/23K
off / std / peak · Hyatt Cat 5
$320/night cash
5 nights = 100,000 pts (~$1,600 value)
Hyatt Centric The Loop Chicago
Hyatt·Boutique, centralCat 5 — boutique Loop, walking to Millennium Park.
21K/25K/29K
off / std / peak · Hyatt Cat 6
$380/night cash
5 nights = 125,000 pts (~$1,900 value)
Trip Strategy — open these cards and the trip is mostly free
Open Sapphire Preferred + World of Hyatt. Park Hyatt Chicago (Cat 6, 35K/night) on Magnificent Mile — bonuses cover 4 nights + RT flight.
75K UR → 18K SW for RT flight + Hyatt transfers for 2 nights
$795/yr annual fee
60K bonus = 1.7 nights at Park Hyatt Chicago + free night cert
$95/yr annual fee
Your out-of-pocket budget for this trip
🚗 L train + walking — great urban transit · vs. $3,250 full cash trip
What to see & do in Chicago, IL
Art Institute of Chicago
SightWorld-class collection — American Gothic, Nighthawks, Monet's Water Lilies.
Architecture River Cruise
Only here90-min boat tour past Chicago's most famous skyscrapers. Best of the city.
Millennium Park + The Bean
SightCloud Gate sculpture is iconic. Free summer concerts at Pritzker Pavilion.
Wrigley Field
SightWatch Cubs in 1914 ballpark — ivy walls, Old Style beer, Wrigleyville bars after.
Lou Malnati's / Giordano's
FoodDeep-dish pizza pilgrimage. Different style at each — try both, settle the debate.
Lakefront Bike Trail
Outdoor18 miles of paved trail along Lake Michigan. Rent bikes anywhere downtown.
Events to know about
- Jul · Aug
Lollapalooza
Late July - early August — 4-day music festival in Grant Park.
- Jul
Taste of Chicago
Mid-July — food festival in Grant Park, dozens of local restaurants.
- Oct
Chicago Marathon
Second Sunday of October — World Marathon Major, 50K runners.
- Mar
St. Patrick's Day River Dyeing
Mid-March — Chicago River dyed green; 100-year tradition.