Chicago
North America · United States
Best Months
Apr, May, Jun, Jul, Aug, Sep, Oct
Rec. Nights
4 nights
Airports
ORD, MDW
Avg. Cash
$52 - $2,112/night
Best Value
11.4¢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 $52 to $2112 per night. Points redemptions offer 11.43+ cents per point value.
Points Hotel Recommendations
12 properties in Chicago bookable with points, sorted by value
| Hotel | Program | Check-in | ||||
|---|---|---|---|---|---|---|
Hyatt Place Munster | Hyatt | 6,500 | $219 | 3.4¢ | May 13 | |
Hyatt Regency O'Hare Chicago | Hyatt | 8,000 | $269 | 3.4¢ | May 13 | |
Fairmont Chicago, Millennium Park | Accor | 17,643 | $406 | 2.3¢ | May 14 | |
Swissôtel Chicago | Accor | 15,399 | $354 | 2.3¢ | May 13 | |
The St. Regis Chicago | Marriott | 101,000 | $2,112 | 2.1¢ | May 13 | |
Sports Illustrated Resorts Chicago | Wyndham | 15,000 | $278 | 1.9¢ | May 13 | |
The Ritz-Carlton, Chicago | Marriott | 93,000 | $1,395 | 1.5¢ | May 13 | |
Days Inn by Wyndham Great Lakes Naval Base | Wyndham | 15,000 | $189 | 1.3¢ | May 13 | |
LondonHouse Chicago, Curio Collection by Hilton | Hilton | 75,000 | $739 | 1.0¢ | May 13 | |
Hilton Garden Inn Chicago McCormick Place | Hilton | 70,000 | $556 | 0.8¢ | May 15 | |
Staybridge Suites Chicago-Oakbrook Terrace | IHG | 29,000 | $199 | 0.7¢ | May 13 | |
Holiday Inn Chicago North-Evanston | IHG | 29,000 | $189 | 0.7¢ | May 13 |
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Transfer Points Strategy
Find the best transfer path for your credit card points
Best Value
If you have Points:
Hyatt Place Munster
Cost6,500 pts/night × 4n = 26,000 Hyatt
Value$876 ÷ 26,000 pts= 3.4¢
Transfer time: Instant
If you have ALL Points:
Fairmont Chicago, Millennium Park
Cost17,643 pts/night × 4n = 70,572 Accor
Value$1,623.16 ÷ 70,572 pts= 2.3¢
Transfer time: Instant
If you have Marriott Bonvoy Points:
The St. Regis Chicago
Cost101,000 pts/night × 4n = 404,000 Marriott
Value$8,448 ÷ 404,000 pts= 2.1¢
Transfer time: Instant
If you have Points:
Sports Illustrated Resorts Chicago
Cost15,000 pts/night × 4n = 60,000 Wyndham
Value$1,112.4 ÷ 60,000 pts= 1.9¢
Transfer time: Instant
If you have Hilton Honors Points:
LondonHouse Chicago, Curio Collection by Hilton
Cost75,000 pts/night × 4n = 300,000 Hilton
Value$2,954.64 ÷ 300,000 pts= 1.0¢
Transfer time: Instant
If you have IHG One Rewards Points:
Staybridge Suites Chicago-Oakbrook Terrace
Cost29,000 pts/night × 4n = 116,000 IHG
Value$794.2 ÷ 116,000 pts= 0.7¢
Transfer time: Instant
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 $52/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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