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$399-$412 -- Chicago: 5-Diamond Mag Mile Luxury, Save 40%
 
Source: The Peninsula Chicago | By Karl Klockars

We've found the best dates to stay at the Peninsula, the only 5-Diamond, 5-Star hotel on the Mag Mile.
Select dates between June-August

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Source: Trump International Hotel & Tower Chicago

We've found the best rates all summer at one of the World's Best Hotels (Travel + Leisure), which can save hundreds off peak summer pricing.
Select dates between June-Sept.

100% (17 ratings)
 
Source: The Langham, Chicago

Rooms at Chicago's best hotel certainly don't come cheap in summer. We've searched the calendar to find the best rates through August.
Select dates through August

 
Source: PUBLIC Chicago

Relax in style at this "achingly sophisticated" (Travel + Leisure) spot
Most weekdays, July-August

 
Source: The Inn At Honey Run

Explore Ohio's Amish Country and save up to 60% at this member-favorite bed-and-breakfast with rooms carved directly into the hillside.
Arrive Sunday-Thursday through Sept. 1, 2016

98% (171 ratings)
 
Source: Hummingbird Inn Bed & Breakfast

Plan a couples escape to the "quaint and restful" Missouri Ozarks, an area "replete with Americana charm" (Conde Nast Traveler).
Travel through Sept. 30, 2016

98% (62 ratings)
 
Source: Lodge of Four Seasons

"Luxurious updates await" (435 Magazine) at the newly refreshed Lodge of Four Seasons, along the picturesque shores of the Lake of the Ozarks.
Sunday-Thursday, May 30 - Oct. 27

90% (372 ratings)
 
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.
Arrive daily through June 16 and Aug. 15 - Oct. 16

 
Source: Audubon Inn

Members can save over 45% at this "charming and elegant" (Madison Magazine) hotel in central Wisconsin, including a spa treatment or dining credit.
Sunday-Friday through Sept. 30, 2016

98% (121 ratings)
 
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.
April 15, 2016 - Sept. 30, 2016

96% (1461 ratings)
 
Source: The Cincinnatian Hotel

Get lost in the old-world charm of the elegant AAA 4-Diamond Cincinnatian Hotel. Members can save over 40% on a stay including valet parking.
Daily through June 30

93% (504 ratings)
 
Source: Gunflint Lodge

Head to the best wilderness resort in Minnesota and get away from civilization for some solitude along the shores of Gunflint Lake.
Travel daily between May 7 - Oct. 23, 2016

96% (188 ratings)
 
Source: Gunflint Outfitters

Visit this "one-million-acre bastion of lakes, streams, and primordial pine forests" (National Geographic) for an unforgettable canoeing adventure.
May 15, 2016 - Oct. 1, 2016

96% (188 ratings)
 

Hotels with Member-Exclusive Extras

 
Source: The Silversmith Hotel

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

100% (11 ratings)
 
Source: Thompson Chicago

The newly renovated luxury hotel debuted in October 2013
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% (67 ratings)
 
Source: Hotel Lincoln

Classically chic hotel right next to Lincoln Park and Lake Michigan
Available year-round

Member Favorite: 96% (101 ratings)
 
Source: The Hotel Minneapolis

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

Member Favorite: 96% (28 ratings)
 
Source: Wyndham Grand Chicago Riverfront

This hotel underwent a multimillion-dollar redesign in 2013
Available year-round

Member Favorite: 96% (406 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% (5 ratings)
 
Source: The Chase Park Plaza

One of the Top 10 Hotels in St. Louis (U.S. News
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

79% (19 ratings)
 
Source: The Edgewater

The original Streamline Moderne-style building hosted stars like Elvis Presley and the Dalai Lama
Available year-round

94% (101 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: Fairfield Inn & Suites Chicago Downtown / Magnificent Mile

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

87% (46 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: 97% (137 ratings)
 
Source: The Plaza Hotel

One of Milwaukee's Top 10 Hotels (TripAdvisor)
Available year-round

81% (26 ratings)
 
Source: Central Loop Hotel

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

93% (15 ratings)
 
Source: Seven Gables Inn

Save 40% at a charming, amenity-heavy St. Louis inn
Available year-round

67% (6 ratings)
 
Source: Chula Vista Resort

Huge 80,000-square-foot indoor water park
Available year-round

90% (166 ratings)
 
Source: Club Quarters Hotel, Wacker at Michigan

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

89% (27 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

80% (45 ratings)
 
Source: River Hotel

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

77% (13 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

 

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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.)