Chicago
North America · United States
Best Months
Apr, May, Jun, Jul, Aug, Sep, Oct
Rec. Nights
4 nights
Airports
ORD, MDW
Avg. Cash
$64.8 - $544/night
Best Value
4.2¢via Hyatt
Overview
Chicago is one of America greatest cities, sitting on the southwestern shore of Lake Michigan with a skyline that rivals New York. The best time to visit is April through October, when warm weather opens up the city famous lakefront, rooftop bars, and outdoor festivals. Summer brings iconic events like Lollapalooza, the Taste of Chicago, and the Chicago Air and Water Show, while spring and fall offer pleasant temperatures with thinner crowds and better hotel rates.
The city is a paradise for architecture lovers — the Chicago Architecture Center boat tour along the Chicago River is consistently rated one of the best tours in the world. Millennium Park and its iconic Cloud Gate sculpture (The Bean) anchor the downtown experience, while Museum Campus houses the Field Museum, Shedd Aquarium, and Adler Planetarium. Neighborhood hopping is essential: Wicker Park for indie vibes, Lincoln Park for green spaces, and the Magnificent Mile for shopping.
For points travelers, Chicago offers exceptional hotel coverage. With 85 properties across Marriott, Hilton, Hyatt, IHG, and Wyndham, the city is one of the deepest award redemption markets in the country. Properties range from the iconic Palmer House Hilton to the modern Hyatt Centric Chicago Magnificent Mile, with options in every neighborhood and price tier.
Cash vs Points
Hotels in Chicago range from $64.8 to $544 per night. Points redemptions offer 4.21+ cents per point value.
Points Hotel Recommendations
10 properties in Chicago bookable with points, sorted by value
| Hotel | Program | ||||
|---|---|---|---|---|---|
Hyatt Place Chicago / Wicker Park | Hyatt | 12,000 | $505 | 4.2¢ | |
Hyatt Regency Schaumburg, Chicago | Hyatt | 5,000 | $206 | 4.1¢ | |
Baymont by Wyndham Schaumburg Chicago Northwest | Wyndham | 15,000 | $399 | 2.7¢ | |
Courtyard by Marriott Chicago Lincolnshire | Marriott | 10,400 | $146 | 1.4¢ | |
Courtyard by Marriott Chicago Oakbrook Terrace | Marriott | 12,500 | $170 | 1.4¢ | |
Harrah's Joliet | Wyndham | 15,000 | $192 | 1.3¢ | |
Holiday Inn Express And Suites Riverwoods | IHG | 16,000 | $127 | 0.8¢ | |
Holiday Inn Hotel And Suites Bolingbrook | IHG | 22,000 | $175 | 0.8¢ | |
Hampton Inn & Suites Chicago Medical District UIC | Hilton | 70,000 | $418 | 0.6¢ | |
Hilton Garden Inn Chicago McCormick Place | Hilton | 70,000 | $401 | 0.6¢ |
Transfer Points Strategy
Find the best transfer path for your credit card points
Best Value
If you have Points:
Hyatt Place Chicago / Wicker Park
HyattHyatt (1:1)Hyatt Place Chicago / Wicker Park
Cost12,000 pts/night × 4n = 48,000 Hyatt
Value$2,020 ÷ 48,000 pts= 4.2¢
Transfer time: Instant
If you have Points:
Baymont by Wyndham Schaumburg Chicago Northwest
WyndhamWyndham (1:1)Baymont by Wyndham Schaumburg Chicago Northwest
Cost15,000 pts/night × 4n = 60,000 Wyndham
Value$1,596 ÷ 60,000 pts= 2.7¢
Transfer time: Instant
If you have Marriott Bonvoy Points:
Courtyard by Marriott Chicago Lincolnshire
MarriottMarriott (1:1)Courtyard by Marriott Chicago Lincolnshire
Cost10,400 pts/night × 4n = 41,600 Marriott
Value$584 ÷ 41,600 pts= 1.4¢
Transfer time: Instant
If you have IHG One Rewards Points:
Holiday Inn Express And Suites Riverwoods
IHGIHG (1:1)Holiday Inn Express And Suites Riverwoods
Cost16,000 pts/night × 4n = 64,000 IHG
Value$509.2 ÷ 64,000 pts= 0.8¢
Transfer time: Instant
If you have Hilton Honors Points:
Hampton Inn & Suites Chicago Medical District UIC
HiltonHilton (1:1)Hampton Inn & Suites Chicago Medical District UIC
Cost70,000 pts/night × 4n = 280,000 Hilton
Value$1,672.08 ÷ 280,000 pts= 0.6¢
Transfer time: Instant
Recommended Activities
Curated experiences in Chicago
Sightseeing
Must-Do
Chicago Architecture Boat Tour
Cruise along the Chicago River while expert guides narrate the stories behind over 40 iconic skyscrapers. Widely regarded as the single best activity in Chicago, this tour showcases why the city is the birthplace of the modern skyscraper.
1.5 hours$47
EveryonePhotography
Sightseeing
Must-Do
Millennium Park & Cloud Gate
Explore Chicago's crown jewel park featuring the legendary Cloud Gate sculpture ("The Bean"), the interactive Crown Fountain, and the Frank Gehry-designed Jay Pritzker Pavilion.
2 hours$0
EveryonePhotography
Cultural
Must-Do
Art Institute of Chicago
Home to Seurat's "A Sunday on La Grande Jatte" and Grant Wood's "American Gothic," this world-class museum holds nearly 300,000 works spanning 5,000 years.
3 hours$35
CultureEveryone
Food
Must-Do
Deep Dish Pizza Experience
Sink your teeth into Chicago's most iconic culinary creation at legendary pizzerias like Lou Malnati's, Giordano's, or Pequod's with its signature caramelized crust.
2 hours$30
FoodiesFamilies
Sightseeing
Skydeck at Willis Tower
Step onto The Ledge, a glass-floored balcony extending from the 103rd floor of the Western Hemisphere's fifth-tallest building. On a clear day, you can see four states.
1.5 hours$41
FamiliesPhotography
Sightseeing
The Second City Comedy Show
Catch a show at the legendary improv theater that launched the careers of Tina Fey, Bill Murray, and Steve Carell. The gold standard of American comedy since 1959.
2 hours$35
CouplesEveryone
Adventure
Lakefront Trail Bike Ride
Rent a Divvy bike and pedal along the 18-mile Lakefront Trail hugging the shore of Lake Michigan, passing North Avenue Beach, Navy Pier, and the Museum Campus.
2.5 hours$15
AdventureEveryone
Cultural
Field Museum of Natural History
Meet SUE, the largest and most complete T. rex fossil ever discovered, then journey through ancient Egypt, gemstone halls, and immersive exhibits on evolution and biodiversity.
3 hours$30
FamiliesCulture
Travel Tips
Best Time to Visit
Apr, May, Jun, Jul, Aug, Sep, Oct
Getting There
ORD, MDW
Visa & Entry
Check your country's requirements
Budget
From $64.8/night
Packing Essentials
Pack for the climate
Cultural Tips
Respect local customs
Ask AI About Chicago
Have questions about traveling to Chicago with points? Our AI advisor can help you plan the perfect trip, compare hotels, and find the best value redemptions.
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