Find the best hotel deals across Marriott, Hilton, Hyatt, IHG, Accor, and more — ranked by total value. Compare cash rates and points redemptions side by side to see which booking method saves you the most. Updated daily with the highest-value hotel bookings worldwide. Book direct through Gondola and earn your hotel loyalty points, credit card points, and 3-7% Gondola Cash back on every reservation.
Find the best hotel points deals in Chicago for January 2027. Compare cash rates and points redemptions across Marriott, Hilton, Hyatt, IHG, Accor, and more, ranked by total value. See which booking method saves you the most. Updated daily with the highest-value hotel bookings in Chicago. Book direct through Gondola and earn your hotel loyalty points, credit card points, and 3-7% Gondola Cash back on every reservation.
Want advanced search?
Create a free account to search every possible use of hotel points and find the best value for your stay in Chicago.
Last updated October 7, 2026
For January 2027, Gondola compared live cash and points rates across Chicago's hotels and narrowed them to the 20 with the best points value, ranked by how far your points go against the cash rate. The strongest points redemption is Chicago Athletic Association, a Hyatt Hotel: 15,000 World of Hyatt points a night for a room that costs $416 in cash, about 2.77 cents per point. For a more everyday stay, Park Hyatt Chicago runs 20,000 World of Hyatt points a night versus $483, around 2.41 cents per point. The Magnificent Mile and Loop have a ton of chain hotel competition, which is great news for points bookings. Some of the best redemption values in the Midwest. Every booking is direct with the hotel, so you keep your hotel loyalty points and status nights, earn your credit card points, and get 3-7% back in Gondola Cash on top of all of it.
| # | Hotel | Points program | Cash / night | Points / night | Value per point |
|---|---|---|---|---|---|
| 1 | Chicago Athletic Association, a Hyatt HotelChicago, Destination Hotels | World of Hyatt | $416 | 15,000 | 2.77¢ |
| 2 | Park Hyatt ChicagoChicago, Park Hyatt | World of Hyatt | $483 | 20,000 | 2.41¢ |
| 3 | Hyatt Regency ChicagoChicago, Hyatt Regency | World of Hyatt | $282 | 12,000 | 2.35¢ |
| 4 | Thompson Chicago, by HyattChicago, Thompson Hotels | World of Hyatt | $550 | 25,000 | 2.20¢ |
| 5 | Hyatt Regency McCormick Place ChicagoChicago, Hyatt Regency | World of Hyatt | $253 | 12,000 | 2.11¢ |
| 6 | Hotel LincolnChicago, Joie De Vivre | World of Hyatt | $143 | 8,000 | 1.79¢ |
| 7 | Radisson Blu Aqua Hotel ChicagoChicago, Radisson Blu - by Choice Hotels | Choice Privileges Rewards | $418 | 30,000 | 1.39¢ |
| 8 | The St. Regis ChicagoChicago, St Regis | Marriott Bonvoy | $869 | 71,000 | 1.22¢ |
| 9 | JW Marriott ChicagoChicago, JW Marriott | Marriott Bonvoy | $577 | 48,000 | 1.20¢ |
| 10 | Marriott Marquis ChicagoChicago, Marriott Hotels & Resorts | Marriott Bonvoy | $569 | 48,000 | 1.19¢ |
| 11 | InterContinental Chicago Magnificent Mile, an IHG HotelChicago, Inter-Continental | IHG One Rewards | $872 | 76,000 | 1.15¢ |
| 12 | The Westin Michigan Avenue ChicagoChicago, Westin | Marriott Bonvoy | $460 | 42,000 | 1.10¢ |
| 13 | The Midland Hotel, Chicago, A Tribute Porfolio HotelChicago, W Hotels | Marriott Bonvoy | $407 | 39,000 | 1.04¢ |
| 14 | W Chicago - LakeshoreChicago, W Hotels | Marriott Bonvoy | $331 | 35,000 | 0.95¢ |
| 15 | The Westin Chicago River NorthChicago, Westin | Marriott Bonvoy | $391 | 42,000 | 0.93¢ |
| 16 | Sheraton Grand Chicago RiverwalkChicago, Sheraton Hotel | Marriott Bonvoy | $439 | 48,500 | 0.91¢ |
| 17 | The LaSalle Chicago, Autograph CollectionChicago, Autograph Collection Hotels & Resorts | Marriott Bonvoy | $456 | 52,000 | 0.88¢ |
| 18 | theWit Chicago, a Hilton HotelChicago, Hilton Hotels | Hilton Honors | $645 | 75,000 | 0.86¢ |
| 19 | Renaissance Chicago O'Hare Suites HotelChicago, Renaissance | Marriott Bonvoy | $233 | 28,000 | 0.83¢ |
| 20 | Hotel Chicago Downtown, Autograph Collection by MarriottChicago, Autograph Collection Hotels & Resorts | Marriott Bonvoy | $424 | 52,000 | 0.82¢ |
It depends on the property. Gondola ranks each hotel by its points value, shown as cents per point in the table above. The higher that number, the more you get by redeeming points instead of paying cash.The Magnificent Mile and Loop have a ton of chain hotel competition, which is great news for points bookings. Some of the best redemption values in the Midwest.
Right now it is Chicago Athletic Association, a Hyatt Hotel at about 2.77 cents per point, redeeming 15,000 World of Hyatt points for a night that would otherwise cost $416.
Yes. Gondola books directly with the hotel, so you keep your hotel loyalty points and status nights and earn your credit card points. On top of all of that, you get 3-7% back in Gondola Cash, where $1 in Gondola Cash equals $1 toward your next hotel booking.
Gondola refreshes these rankings regularly from live rate data. This page was last updated October 7, 2026.
Gondola runs a free MCP server that connects hotel search and booking directly to AI assistants like ChatGPT, Claude, Cursor, and other MCP clients. Ask for Chicago points deals in plain language and get live member rates with cash and points side by side, including the cents-per-point value shown above. Add it to your AI client at mcp.gondola.ai/mcp/auth. Your client will ask you to sign in to Gondola through OAuth before it calls a tool.
Set up the Gondola MCP server