Weekend getaways from Chicago

Weekend: gas $26 ($4.14 a gallon, 77 miles each way), hotel rooms for two $244 (off season in November 2026), food and fun $570. All estimates; how WRLD estimates.

Weekend: gas $31 ($4.14 a gallon, 94 miles each way), hotel rooms for two $222, food and fun $480. All estimates; how WRLD estimates.

Weekend: gas $32 ($4.14 a gallon, 98 miles each way), hotel rooms for two $255, food and fun $480. All estimates; how WRLD estimates.

Weekend: gas $36 ($4.14 a gallon, 109 miles each way), hotel rooms for two $244 (off season in November 2026), food and fun $570. All estimates; how WRLD estimates.

Weekend: gas $40 ($4.14 a gallon, 120 miles each way), hotel rooms for two $217 (off season in November 2026), food and fun $480. All estimates; how WRLD estimates.

Weekend: gas $43 ($4.14 a gallon, 130 miles each way), hotel rooms for two $192 (off season in November 2026), food and fun $480. All estimates; how WRLD estimates.

Also free: Musical Fountain shows on summer nights.

Weekend: gas $47 ($4.14 a gallon, 141 miles each way), hotel rooms for two $219 (off season in November 2026), food and fun $480. All estimates; how WRLD estimates.

Weekend: gas $58 ($4.14 a gallon, 174 miles each way), hotel rooms for two $192 (off season in November 2026), food and fun $480. All estimates; how WRLD estimates.

Weekend: gas $62 ($4.14 a gallon, 186 miles each way), hotel rooms for two $192 (off season in November 2026), food and fun $480. All estimates; how WRLD estimates.

Weekend: gas $65 ($4.14 a gallon, 195 miles each way), hotel rooms for two $192 (off season in November 2026), food and fun $480. All estimates; how WRLD estimates.

Weekend: gas $70 ($4.14 a gallon, 212 miles each way), hotel rooms for two $192 (off season in November 2026), food and fun $480. All estimates; how WRLD estimates.

Weekend: gas $79 ($4.14 a gallon, 239 miles each way), hotel rooms for two $213 (off season in November 2026), food and fun $480. All estimates; how WRLD estimates.

Weekend: gas $81 ($4.14 a gallon, 243 miles each way), hotel rooms for two $192 (off season in November 2026), food and fun $480. All estimates; how WRLD estimates.

Weekend: gas $88 ($4.14 a gallon, 266 miles each way), hotel rooms for two $192 (off season in November 2026), food and fun $480. All estimates; how WRLD estimates.

Weekend: gas $89 ($4.14 a gallon, 268 miles each way), hotel rooms for two $269 (off season in November 2026), food and fun $570. All estimates; how WRLD estimates.

Weekend: gas $89 ($4.14 a gallon, 269 miles each way), hotel rooms for two $257 (off season in November 2026), food and fun $570. All estimates; how WRLD estimates.

Weekend: gas $90 ($4.14 a gallon, 270 miles each way), hotel rooms for two $279 (off season in November 2026), food and fun $570. All estimates; how WRLD estimates.

Weekend: gas $94 ($4.14 a gallon, 283 miles each way), hotel rooms for two $244 (off season in November 2026), food and fun $570. All estimates; how WRLD estimates.

Weekend: gas $94 ($4.14 a gallon, 284 miles each way), hotel rooms for two $244 (off season in November 2026), food and fun $570. All estimates; how WRLD estimates.

Weekend: gas $96 ($4.14 a gallon, 289 miles each way), hotel rooms for two $244 (off season in November 2026), food and fun $570. All estimates; how WRLD estimates.

Weekend: gas $96 ($4.14 a gallon, 291 miles each way), hotel rooms for two $244 (off season in November 2026), food and fun $570. All estimates; how WRLD estimates.

Weekend: gas $96 ($4.01 a gallon, 298 miles each way), hotel rooms for two $244 (off season in November 2026), food and fun $570. All estimates; how WRLD estimates.

Long weekend: gas $105 ($4.14 a gallon, 318 miles each way), hotel rooms for two $289 (off season in November 2026), food and fun $640. All estimates; how WRLD estimates.

Long weekend: gas $106 ($4.14 a gallon, 319 miles each way), hotel rooms for two $366 (off season in November 2026), food and fun $760. All estimates; how WRLD estimates.

Also free: South Pier lighthouse and Michigan Beach.

Long weekend: gas $110 ($4.14 a gallon, 331 miles each way), hotel rooms for two $376 (off season in November 2026), food and fun $760. All estimates; how WRLD estimates.

Also free: Little Traverse Wheelway bike trail.

Long weekend: gas $110 ($4.14 a gallon, 331 miles each way), hotel rooms for two $289 (off season in November 2026), food and fun $640. All estimates; how WRLD estimates.

Long weekend: gas $111 ($4.14 a gallon, 334 miles each way), hotel rooms for two $500 (off season in November 2026), food and fun $920. All estimates; how WRLD estimates.

Long weekend: gas $111 ($4.14 a gallon, 335 miles each way), hotel rooms for two $289 (off season in November 2026), food and fun $640. All estimates; how WRLD estimates.

Long weekend: gas $121 ($4.14 a gallon, 365 miles each way), hotel rooms for two $289 (off season in November 2026), food and fun $640. All estimates; how WRLD estimates.

Long weekend: gas $122 ($4.14 a gallon, 367 miles each way), hotel rooms for two $289 (off season in November 2026), food and fun $640. All estimates; how WRLD estimates.

Also free: Mackinac Bridge views from the shoreline parks.

Long weekend: gas $124 ($4.14 a gallon, 373 miles each way), hotel rooms for two $289 (off season in November 2026), food and fun $640. All estimates; how WRLD estimates.

Long weekend: gas $124 ($4.14 a gallon, 375 miles each way), hotel rooms for two $558 (off season in November 2026), food and fun $920. All estimates; how WRLD estimates.

Long weekend: gas $126 ($4.14 a gallon, 380 miles each way), hotel rooms for two $289 (off season in November 2026), food and fun $640. All estimates; how WRLD estimates.

Long weekend: gas $128 ($4.14 a gallon, 387 miles each way), hotel rooms for two $289 (off season in November 2026), food and fun $640. All estimates; how WRLD estimates.

Also free: Sugarloaf Mountain hike.

Long weekend: gas $130 ($4.14 a gallon, 392 miles each way), hotel rooms for two $289 (off season in November 2026), food and fun $640. All estimates; how WRLD estimates.

Long weekend: gas $131 ($4.14 a gallon, 396 miles each way), hotel rooms for two $304 (off season in November 2026), food and fun $640. All estimates; how WRLD estimates.

Long weekend: gas $140 ($4.14 a gallon, 423 miles each way), hotel rooms for two $289 (off season in November 2026), food and fun $640. All estimates; how WRLD estimates.

Long weekend: gas $142 ($4.17 a gallon, 425 miles each way), hotel rooms for two $485, food and fun $760. All estimates; how WRLD estimates.

Long weekend: gas $143 ($4.14 a gallon, 430 miles each way), hotel rooms for two $289 (off season in November 2026), food and fun $640. All estimates; how WRLD estimates.

Long weekend: gas $145 ($4.14 a gallon, 438 miles each way), hotel rooms for two $289 (off season in November 2026), food and fun $640. All estimates; how WRLD estimates.

Weekend: gas $32 ($4.14 a gallon, 96 miles each way), hotel rooms for two $203 (off season in November 2026), food and fun $480. All estimates; how WRLD estimates.

Weekend: gas $55 ($4.14 a gallon, 167 miles each way), hotel rooms for two $192 (off season in November 2026), food and fun $480. All estimates; how WRLD estimates.

Weekend: gas $59 ($4.14 a gallon, 178 miles each way), hotel rooms for two $255, food and fun $480. All estimates; how WRLD estimates.

Weekend: gas $79 ($4.14 a gallon, 238 miles each way), hotel rooms for two $255, food and fun $480. All estimates; how WRLD estimates.

Weekend: gas $88 ($4.14 a gallon, 266 miles each way), hotel rooms for two $247, food and fun $480. All estimates; how WRLD estimates.

Weekend: gas $98 ($4.14 a gallon, 297 miles each way), hotel rooms for two $255, food and fun $480. All estimates; how WRLD estimates.

Long weekend: gas $105 ($4.14 a gallon, 316 miles each way), hotel rooms for two $320 (off season in November 2026), food and fun $640. All estimates; how WRLD estimates.

Long weekend: gas $122 ($4.01 a gallon, 379 miles each way), hotel rooms for two $304 (off season in November 2026), food and fun $640. All estimates; how WRLD estimates.

Also free: Brandywine Falls.

Long weekend: gas $122 ($4.01 a gallon, 381 miles each way), hotel rooms for two $382, food and fun $640. All estimates; how WRLD estimates.

Long weekend: gas $133 ($4.14 a gallon, 401 miles each way), hotel rooms for two $304 (off season in November 2026), food and fun $640. All estimates; how WRLD estimates.

Long weekend: gas $133 ($4.14 a gallon, 402 miles each way), hotel rooms for two $371, food and fun $640. All estimates; how WRLD estimates.

Long weekend: gas $137 ($4.14 a gallon, 414 miles each way), hotel rooms for two $304 (off season in November 2026), food and fun $640. All estimates; how WRLD estimates.

Long weekend: gas $141 ($4.14 a gallon, 424 miles each way), hotel rooms for two $320 (off season in November 2026), food and fun $640. All estimates; how WRLD estimates.

Weekend: gas $50 ($4.14 a gallon, 150 miles each way), hotel rooms for two $255, food and fun $480. All estimates; how WRLD estimates.

Weekend: gas $66 ($4.14 a gallon, 198 miles each way), hotel rooms for two $255, food and fun $480. All estimates; how WRLD estimates.

Weekend: gas $97 ($4.01 a gallon, 303 miles each way), hotel rooms for two $255, food and fun $480. All estimates; how WRLD estimates.

Weekend: gas $104 ($4.14 a gallon, 315 miles each way), hotel rooms for two $255, food and fun $480. All estimates; how WRLD estimates.

Also free: Saint Louis Art Museum.

Long weekend: gas $107 ($4.14 a gallon, 323 miles each way), hotel rooms for two $336, food and fun $640. All estimates; how WRLD estimates.

Long weekend: gas $118 ($4.01 a gallon, 369 miles each way), hotel rooms for two $382, food and fun $640. All estimates; how WRLD estimates.

Weekend: gas $43 ($4.14 a gallon, 130 miles each way), hotel rooms for two $192 (off season in November 2026), food and fun $480. All estimates; how WRLD estimates.

Weekend: gas $80 ($4.14 a gallon, 241 miles each way), hotel rooms for two $296, food and fun $570. All estimates; how WRLD estimates.