1. Home
  2. Hotels
  3. Chicago & Midwest

Chicago & Midwest Hotel Deals

New Hotel Search

Search Deals From Thousands Of Recommended Hotels

Browse Top Deals

$159 -- July 4th at Hotel next to Fair St. Louis Festival
Source: The Chase Park Plaza | By Ryan Haase

Travel Channel says St. Louis' July 4th fireworks are some of the best in the U.S., and they happen across the street
July 4th

More »
Source: Chula Vista Resort

With this holiday weekend sale, receive an exclusive 35% daily discount on Villas and two-bedroom Condos at this critically-praised Dells resort.
June 30 - July 4

90% (166 ratings)
Source: Starwood

Summer is the best time to see everything Chicago has to offer, and rates are now below $200 for three prime location hotels.

Source: The Hotel Minneapolis

This member-fave 4-star spot is just 10 minutes from prime fireworks views, and stays include an exclusive dining credit.
June 30-July 4

96% (28 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

89% (57 ratings)
Source: The Alexander Hotel

Members save 60% on a stay at the Alexander, just a 20-minute walk from the best spot to view the July 4th fireworks.
June 30-July 6

98% (50 ratings)
Source: The Capitol Hotel, an Ascend Hotel Collection Member

We've found the best dates to stay downtown near Music City's restaurants, bars and famous honky tonks, saving up to half off surrounding dates.
Select dates, July-August

Source: The Cincinnatian Hotel

Get lost in the "contemporary elegance" (Fodor's) of the Cincinnatian Hotel while saving 35% on a stay.
June 30-July 4

94% (521 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: The Commons Hotel

This east-bank hotel that Fodor's calls "cozy and quirky" is a 10-minute drive from the Red, White & Boom fest with live music and fireworks.
June 29 - July 10

Source: Hotel Indigo Chicago Downtown Gold Coast

Even in summer, guests can save big on a stay at this "bright and cheery" boutique (Gayot) near Oak Street Beach.
Select weekdays through Sept. 1

100% (5 ratings)
Source: The Plaza Hotel, Milwaukee

One of Milwaukee's Top 10 Hotels (TripAdvisor), the Plaza offers members exclusive extras like parking and credit to the recently-renovated cafe.
Travel weekdays through October

Source: The Brown Hotel

This "grand-but-intimate" property (Fodor's) is one of Travel + Leisure's World's Best Hotels. Travelzoo members can save 55% on a stay.
Daily between July 1 - Sept. 20, 2016

96% (83 ratings)
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% (1501 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 through Oct. 23, 2016

96% (197 ratings)
Source: Gunflint Outfitters

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

96% (197 ratings)

Hotels with Member-Exclusive Extras

Source: The Silversmith Hotel

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

100% (12 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% (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: 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% (406 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

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% (47 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: 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

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% (27 ratings)
Source: Westin St. Louis

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

Source: River Hotel

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

80% (15 ratings)
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


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.)