1. Home
  2. Hotels
  3. Chicago & Midwest

Chicago & Midwest Hotel Deals

New Hotel Search

Search Deals From Thousands Of Recommended Hotels

Browse Top Deals

$279 -- Virginia: 'Top Romantic Inn in the Nation', Save 35%
Source: Goodstone Inn & Restaurant | By Karl Klockars

Retire to D.C.'s Wine Country for a stay at the Goodstone Inn & Restaurant, one of Conde Nast Traveler's Top 30 Hotels in the South.
Sunday-Thursday through Sept. 29, 2016

More »
100% (50 ratings)
Source: Chateau on the Lake Resort

The only AAA 4-Diamond resort in Branson is offering Travelzoo members exclusive 50% savings on late-summer and early fall travel.
Travel through Dec. 30

95% (330 ratings)
Source: Dollywood's DreamMore Resort

Find yourself a new "Tennessee Mountain Home" this summer with a stay at this family-friendly spot near the Dollywood theme park.
Weekdays Aug. 15 - Sept. 29; +50 for weekends

Source: Hotel Lincoln

Members can lock in exclusive savings through 2016 at this Lincoln Park spot, named one of Chicago's Best Boutique Hotels (Travel + Leisure).
Select weekdays throughout 2016

96% (101 ratings)
Source: Chula Vista Resort

Members can save 35% on a late-summer trip to the Dells when they reserve a stay at the member-fave Chula Vista Resort.
Through Oct. 31

90% (173 ratings)
Source: Great Wolf Lodge Sandusky

All stays at the Great Wolf Lodge in Sandusky include daily access to the indoor waterpark
Midweek through summer; weekends also discounted

100% (5 ratings)
Source: Put-in-Bay Resort and Conference Center

Grab a few friends and head to Put-in-Bay, described as the "Key West of the Great Lakes" by The New York Times, during peak beach season.
Sunday-Thursday through August 31

90% (67 ratings)
Source: Bay Lodging Resort

Put-in-Bay on South Bass Island is an "easy and family-friendly island escape" that offers history and "lots of family fun" (Travel + Leisure).
Sunday-Thursday through Aug. 31

Source: French Broad River Dude Ranch

Unpack that 10-gallon Stetson, break out your best pair of boots and get ready for an all-inclusive dude ranch experience in the Smoky Mountains.
Select arrival dates between June 5 - Aug. 28

Source: The Lodge at Mount Rushmore

The "majestic" Mt. Rushmore is one of "America's most beautiful landmarks" (Travel + Leisure). Travelzoo members save up to half on a two-night stay.
Travel between June 17-July 17 or Aug. 15-Oct. 16

Source: State House Inn, an Ascend Collection hotel

Save over 50% at this member-favorite hotel with midcentury-modern style; it's a great destination for a Springfield stay full of history.
Daily through Sept. 30, 2016

96% (1562 ratings)

Hotels with Member-Exclusive Extras

Source: The Silversmith Hotel

One block from the public art playground of Millennium Park
Available year-round

100% (14 ratings)
Source: Thompson Chicago

This AAA 4 Diamond hotel is known for having great service
Available year-round

100% (18 ratings)
Source: Hotel Chicago Downtown

A hip, high-energy hotel adjacent to Chicago's House of Blues
Available year-round

93% (68 ratings)
Source: The Hotel Minneapolis

Occupies a 1906 building that originally opened as a bank
Available year-round

Member Favorite: 97% (29 ratings)
Source: Wyndham Grand Chicago Riverfront

This AAA 4 Diamond hotel has a convenient riverfront location a block from Magnificent Mile
Available year-round

Member Favorite: 96% (408 ratings)
Source: The Chase Park Plaza

One of the Top 10 Hotels in St. Louis (U.S. News
Available year-round

83% (18 ratings)
Source: The Cincinnatian Hotel

The "city’s grandest hotel" according to Travel + Leisure
Available year-round

94% (536 ratings)
Source: The Commons Hotel, A Noble House Hotel

A top-to-toe renovated hotel on University of Minnesota’s campus
Available year-round

80% (10 ratings)
Source: Radisson Blu Aqua Hotel, Chicago

Ranked one of the Best Hotels in Chicago in the Conde Nast Traveler Readers’ Choice Awards 2014
Available year-round

100% (12 ratings)
Source: HotelRED

Named the city's best hotel (Madison Magazine 2015 Readers' Poll)
Available year-round

Member Favorite: 96% (27 ratings)
Source: St. Louis City Center Hotel

Housed in a 1929 landmark building in the heart of downtown St. Louis
Available year-round

80% (20 ratings)
Source: The Edgewater

The Edgewater is the only AAA 4-Diamond hotel in Madison
Available year-round

93% (104 ratings)
Source: Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

Bargain pick in an upscale, central neighborhood
Available year-round

88% (48 ratings)
Source: Best Western Plus Hawthorne Terrace

Located in the Lakeview neighborhood; Wrigley Field, Lake Michigan, Lincoln Park and dozens of restaurants and bars are walkable
Available year-round

100% (10 ratings)
Source: IVY Boutique Hotel

A cool boutique hotel within walking distance to many of Chicago’s most popular attractions
Available year-round

Member Favorite: 96% (138 ratings)
Source: Chicago Athletic Association

Stay in a palatial building that was once a private club for the city's elite
Available year-round

Member Favorite: 98% (81 ratings)
Source: The Plaza Hotel

One of Milwaukee's top 10 hotels (TripAdvisor)
Available year-round

83% (30 ratings)
Source: Central Loop Hotel

Located in the center of The Loop in the heart of Chicago’s business district
Available year-round

95% (19 ratings)
Source: Seven Gables Inn

Extras that other hotels may charge for, like Wi-Fi access and bottled water, are complimentary
Available year-round

67% (6 ratings)
Source: Club Quarters Hotel, Wacker at Michigan

One block from the shopping mecca of Magnificent Mile
Available year-round

89% (28 ratings)
Source: River Hotel

Steps from the start of Chicago’s Magnificent Mile 
Available year-round

82% (17 ratings)
Source: Westin St. Louis

Revamped historic warehouse building in downtown, next to Cardinals’ Busch Stadium
Available year-round

Source: Club Quarters Hotel, Central Loop

Less than four blocks from the Willis Tower and the Art Institute of Chicago 
Available year-round

78% (46 ratings)
Source: Westin Minneapolis

AAA 4-Diamond Art Deco hotel – set in a former Minneapolis bank
Available year-round

Source: Courtyard Marriott Country Club Plaza

Ideal location right on the Plaza
Available year-round

Source: The Iron Horse Hotel

One of Travel + Leisure's World's Best Hotels for 2015
Available year-round

Source: The Cheshire

The original owner gave it Tudoresque touches, like wood beams and stained-glass windows
Available year-round

Source: Hilton Minneapolis/Bloomington Hotel

Good-value hotel with courteous staff and comfy rooms
Available year-round


More Deals on Chicago & Midwest Hotels


Compare Multiple Travel Sites in One Search

From: To: Travelers:
Depart: Return: One-way
Enter city: Guests:
Check-in: Check-out: Rooms:
From: To: Travelers:
Depart: Return: Rooms:
Enter city: Pick-up Time:
Pick-up Date: Return Date: Return Time:

Finding Chicago Hotel Deals
A true metropolis, Chicago is one of the nation’s top travel destinations -- and rightfully so. With some of the world’s best museums, architecture, dining and entertainment options, along with amazing parks, lakefront beaches and the many neighborhoods that form the city’s patchwork of population, there’s as many reasons to visit Chicago as there are steps and windows in the Willis Tower.

First time visitors to Chicago (we don’t ever call it Chi-Town) will want to spend at least a couple days exploring the Loop’s architecture, the Magnificent Mile shopping spots and the many downtown open spaces – Millennium and Grant Park are must-sees, which lead you right into the Museum Campus with the Field Museum, Adler Planetarium and the Shedd Aquarium. Navy Pier is most assuredly a touristy place, but it makes for a good skyline photograph (though the view from the Planetarium is much better).

Repeat visitors should absolutely get on the El and explore some of the neighborhoods that make the city such a rich place – places like Lincoln Park, Wicker Park and Lakeview (home of Wrigleyville) are all just minutes from downtown on the Blue or Red lines.

Nelson Algren called Chicago “an October sort of city even in spring” but there’s really never a bad time to visit – the city’s peak season runs basically from April through November, and then hotel prices drop significantly during the chilly winters, making it a great time to visit on a budget.

Visitors will likely feel obligated to sample a deep-dish pizza – and they should, at least once – but too many people leave the city without sampling its true culinary gem, the Italian beef. Don’t make that mistake. (There’s also lots of good thin-crust pizza here, too, for whatever it’s worth.)