We’re learning how we can still explore the Windy City of Chicago while still staying safe. We’re chatting with Max of The Peninsula Chicago and Captain Tom from Chicago’s First Lady Cruises!
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Cheap Flights to Chicago
| Origin | Departure at | Return at | Find tickets |
|---|---|---|---|
| Miami | April 27, 2024 | April 30, 2024 | Fly From 74 |
| New York | May 4, 2024 | May 7, 2024 | Fly From 78 |
| San Diego | May 18, 2024 | May 20, 2024 | Fly From 99 |
| Baltimore | May 2, 2024 | May 4, 2024 | Fly From 125 |
| Ontario | May 14, 2024 | May 17, 2024 | Fly From 126 |
| Los Angeles | May 14, 2024 | May 17, 2024 | Fly From 128 |
| Fort Lauderdale | April 27, 2024 | April 30, 2024 | Fly From 135 |
| Philadelphia | April 20, 2024 | April 21, 2024 | Fly From 137 |
| San Francisco | April 26, 2024 | April 29, 2024 | Fly From 172 |
| Louisville | May 4, 2024 | May 6, 2024 | Fly From 172 |
| Sacramento | May 2, 2024 | May 5, 2024 | Fly From 216 |
| Oakland | April 26, 2024 | April 29, 2024 | Fly From 230 |
| Washington | April 25, 2024 | April 28, 2024 | Fly From 238 |
| Little Rock | May 18, 2024 | May 23, 2024 | Fly From 249 |
| Tampa | April 19, 2024 | April 21, 2024 | Fly From 251 |
| Mexico City | September 25, 2024 | September 30, 2024 | Fly From 264 |
| Charlottesville | July 6, 2024 | July 10, 2024 | Fly From 266 |
| Buffalo | August 4, 2024 | August 6, 2024 | Fly From 285 |
| Montreal | May 6, 2024 | May 10, 2024 | Fly From 296 |
| Thunder Bay | May 11, 2024 | May 15, 2024 | Fly From 351 |
| Vancouver | May 6, 2024 | May 10, 2024 | Fly From 374 |
| Tijuana | April 25, 2024 | April 28, 2024 | Fly From 389 |
| Muscle Shoals | April 18, 2024 | April 22, 2024 | Fly From 460 |
| Barcelona | October 10, 2024 | October 16, 2024 | Fly From 484 |
| Warsaw | April 23, 2024 | April 29, 2024 | Fly From 540 |
| Vilnius | May 9, 2024 | May 15, 2024 | Fly From 552 |
| Vienna | April 23, 2024 | April 29, 2024 | Fly From 571 |
| Istanbul | October 11, 2024 | October 16, 2024 | Fly From 573 |
| Tallinn | June 5, 2024 | June 10, 2024 | Fly From 661 |
| Belgrade | July 17, 2024 | July 21, 2024 | Fly From 673 |
Hotels in Chicago
| Hotel | Stars | Discount | Price before and discount | Select dates |
|---|---|---|---|---|
| Trump International Hotel & Tower Chicago | ★★★★★ | -19% | 489 394 | View Hotel |
| Sofitel Chicago Magnificent Mile | ★★★★★ | -36% | 327 209 | View Hotel |
| Nobu Hotel Chicago | ★★★★★ | -38% | 578 357 | View Hotel |
| Park Hyatt Chicago | ★★★★★ | -18% | 526 433 | View Hotel |
| The Langham Chicago | ★★★★★ | -39% | 603 370 | View Hotel |
| JW Marriott Chicago | ★★★★★ | -59% | 433 177 | View Hotel |
| Waldorf Astoria Chicago | ★★★★★ | -11% | 510 454 | View Hotel |
| Four Seasons Chicago | ★★★★★ | -31% | 588 406 | View Hotel |
| Viceroy Chicago | ★★★★★ | -48% | 458 240 | View Hotel |
| The Peninsula Chicago | ★★★★★ | -41% | 619 367 | View Hotel |
