Follow us:

Sherman's Travel

Hand-Picked Deals, Expert Advice

Great Hotel Deals vetted by our Experts

Chicago and Midwest — Whether you’re looking for accommodations on the Magnificent Mile or the Loop, our travel deal experts have picked a selection of amazing Chicago & Midwest hotel deals you can’t pass up.
Find hotel Deals in Popular Destinations
- Las Vegas
- Florida
- New York City
- California
- Hawaii
- Washington, D.C.
- Chicago & Midwest
- Northeast
- Southern U.S.
- Mountain & West
- Caribbean
- Mexico
- Europe
- Canada
- International

Featured Chicago and Midwest Hotel Deals

from

$155

per night

Chicago: Last-Minute Stay at Stylish 4-Diamond Hotel

from

$52

per night

Hotels in Major U.S. Cities in Summer, Save 45%

Hand-Picked Chicago and Midwest Hotel Deals

from

$255

per night

Chicago: Summer Rates at 4-Diamond Downtown Hotel

Btn_deals_getdetails

theWit Hotel Chicago – A DoubleTree By Hilton

from

$32

per night

Minneapolis: Hotels near Mall of America & Downtown, Save 65%

Btn_deals_getdetails

from

$29

per night

Downtown St. Louis Hotels in Summer, Save 45%

Btn_deals_getdetails

from

$159

per night

Chicago: Downtown Hotel near The Loop

Btn_deals_getdetails

from

$215

per night

Chicago: Luxury Hotel near Magnificent Mile in July

Btn_deals_getdetails

from

$47

per night

Downtown Chicago Hotels in Summer, Save 45%

Btn_deals_getdetails

from

$43

per night

Ohio: Sandusky Hotels near Cedar Point, Save 50%

Btn_deals_getdetails

from

$395

per night

Illinois: Northbrook 4-Star Hotel

Btn_deals_getdetails

from

$333

per night

Missouri: Clayton 3.5-Star Hotel

Btn_deals_getdetails

from

$282

per night

Illinois: Darien 3.5-Star Hotel

Btn_deals_getdetails

from

$99

per night

Saint Louis: Downtown 4-Star Casino Hotel, Save 40%

Btn_deals_getdetails

from

$385

per night

Minnesota: White Bear Lake 3-Star Hotel

Btn_deals_getdetails

from

$283

per night

United States: Chicago 4.5-Star Hotel

Btn_deals_getdetails

from

$70

per night

Chicago: Super 8 Delavan Hotel in July

Btn_deals_getdetails

from

$73

per night

Chicago: Comfort Inn Hoffman Estates in July

Btn_deals_getdetails

from

$76

per night

Chicago: Super 8 Kenosha/Pleasant Prairie Hotel in July

Btn_deals_getdetails

from

$78

per night

Chicago: Country Inn & Suites By Carlson in July, Save 20%

Btn_deals_getdetails

from

$80

per night

Chicago: Best Western Naperville Inn in July

Btn_deals_getdetails

from

$84

per night

Chicago: Baymont Inn & Suites Peoria in July

Btn_deals_getdetails

from

$85

per night

Chicago: Country Inn & Suites By Carlson in July

Btn_deals_getdetails

Compare Rates to Chicago and Midwest

Jaymie_degaetano

“Early morning flights often have lower fares than midday departures.”

Jaymie DeGaetano Travel Deal Expert

Sign up for the Top 25 Newsletter
to get exclusive weekly deals